Chemistry Level) (CIE) Paper 1

CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced LevelCHEMISTRY PAPER 1 Multiple Choice 9701/1 MAY/JUNE SESSION 2002 1 hour Candidates answer on the question paper. Additional materials: Multiple Choice answer sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet TIME 1 hour INSTRUCTIONS TO CANDIDATES Do not open this booklet until you are told to do so. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has already been done for you. There are forty questions in this paper. Answer all questions. For each question there are four possible answers, A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read very carefully the instructions on the answer sheet. INFORMATION FOR CANDIDATES Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This question paper consists of 13 printed pages and 3 blank pages. SB (SC/KN) S16461/4 © CIE 2002 http://www.xtremepapers.net [Turn over 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 0 –1X 1 In the radioactive decay of an isotope of lead to an isotope of bismuth, a particle Which particle is A B C D electron ion neutron proton 0 –1X? is emitted. 2 As a simplification, an adult human can be considered to have a daily diet of 1.80 kg of carbohydrate (empirical formula CH2O). Which mass of carbon dioxide does a person produce each day if all the carbohydrate eaten is digested and oxidised? A 0.267 kg B 0.800 kg C 1.32 kg D 2.64 kg 3 The diagram shows the mass spectrum of a sample of naturally-occurring copper. 7 6 5 relative abundance 4 3 2 1 61 62 63 64 65 66 67 68 m/e What is the relative atomic mass of this copper? A 63.3 B 63.5 C 63.6 D 64.0 9701/1/M/J/02 3 4 A slow stream of water from a tap can be deflected by an electrostatically charged plastic rod because water is a polar molecule. liquid burette negatively charged rod Why is a water molecule polar? A B C D Molecules are bonded together by hydrogen bonds. The oxygen and hydrogen atoms have different electronegativities. The oxygen atom has two lone pairs of electrons. Water is able to dissociate into ions. 5 Why does copper wire conduct electricity when a potential difference is applied? A B C D Bonding electrons in the crystal lattice move. Copper(II) ions move to the cathode. The atoms of copper become ionised. The crystal lattice breaks down. 6 Flask X contains 1 dm3 of helium at 2 kPa pressure and flask Y contains 2 dm3 of neon at 1 kPa pressure. If the flasks are connected at constant temperature, what is the final pressure? A 1 kPa B 1 kPa C 1 kPa D 2 kPa 9701/1/M/J/02 [Turn over 4 7 When heated, solid iodine readily forms iodine vapour. What does this information suggest about the nature of the particles in these two physical states of iodine? solid A B ionic ionic vapour atomic molecular atomic molecular C molecular D molecular 8 Which statement about the standard enthalpy change of formation of carbon dioxide is correct? A B C D It is equal to the standard enthalpy change of combustion of carbon. It is equal to twice the bond energy of the C=O bond. It is the energy released when one mole of carbon dioxide is formed from carbon at the temperature of combustion of the carbon. It is the same for carbon dioxide produced from graphite and from diamond. 9 Use of the Data Booklet is relevant to this question. Hydrazine was used as a fuel for the Messerschmidt 163 rocket fighter in World War II and for the American Gemini and Apollo spacecraft. It has the following formula. H N H N H H What is the enthalpy change of atomisation of 1 mol of gaseous hydrazine? A B C D 550 kJ 1720 kJ 1970 kJ 2554 kJ 10 For which equilibrium does Kc have no units? A B C D C(s) + H2O(g) CO(g) + H2(g) CH3CO2CH3(l) + H2O(l) Cu(NH3)2+(aq) 4 CH3OH(l) + CH3CO2H(l) Cu2+(aq) + 4NH3(aq) N2O4(g) 2NO2(g) 9701/1/M/J/02 5 11 Which curve is obtained if the rate of reaction is plotted against time for an autocatalytic reaction (i.e. a reaction in which one of the products catalyses the reaction)? A B C D rate rate rate rate 0 0 0 time 0 0 time 0 0 time 0 time 12 Which species represented by the following formulae has the largest radius? A P3– B Cl – C Ar D K+ 13 Which of the following oxides is unlikely to dissolve in aqueous sodium hydroxide? A Al 2O3 B MgO C SO2 D SiO2 14 An element of the third period (Na to S) is heated in chlorine. The product is purified and then added to water. The resulting solution is found to be neutral. What is the element? A B C D sodium aluminium silicon phosphorus 15 Which equation represents the reaction that occurs when calcium nitrate is heated strongly? A B C D Ca(NO3)2 → Ca(NO2)2 + O2 Ca(NO3)2 → CaO + N2O + 2O2 Ca(NO3)2 → CaO2 + 2NO2 2Ca(NO3)2 → 2CaO + 4NO2 + O2 9701/1/M/J/02 [Turn over 6 16 During electrolysis of brine in a diaphragm cell, chlorine, hydrogen and sodium hydroxide are produced. What is the molar ratio of these products? chlorine A B C D 1 1 2 2 hydrogen 1 1 1 2 sodium hydroxide 1 2 1 1 17 Which statement explains the observation that magnesium hydroxide dissolves in aqueous ammonium chloride, but not in aqueous sodium chloride? A B C D + The ionic radius of the NH4 ion is similar to that of Mg2+ but not that of Na+. NH4Cl dissociates less fully than NaCl. The ions Na+ and Mg2+ are isoelectronic (have the same number of electrons). + The ion NH4 acts as an acid. 18 Sulphur dioxide is an important food preservative. What property makes sulphur dioxide useful in this role? A B C D It is a gas. It is a reducing agent. It reacts with oxygen to form sulphur trioxide. It reacts with water to form an acidic solution. 19 The anaesthetic halothane, CF3CHBrCl , is made industrially as shown below. HF Br2 CCl2=CHCl → CF3CH2Cl → CF3CHBrCl stage 1 stage 2 What type of reaction is occurring in stage 2? A B C D electrophilic addition electrophilic substitution free radical substitution nucleophilic addition 9701/1/M/J/02 7 20 Which set of alcohols correctly shows a primary, a secondary and a tertiary alcohol? primary CH2OH A CH2 CH3 CH2OH B CH3 C CH3 CH2OH C CH3 C H H D CH3 C H OH CH3 H CH3 H CH3 secondary CH2OH CHOH CH3 CH3 C CH3 CH2OH C H CH3 C H OH CH3 CH2OH CH3 OH CH3 tertiary CH2OH CHOH CH2OH CH3 C H CH2OH CH2OH C CH2OH CH2OH CH3 C CH3 OH 21 What is the total number of different chloroethanes (formula C2H6-nCln, where n can be any integer from 1 to 6)? A 6 B 8 C 9 D 10 22 Polymerisation of chloroethene gives pvc. How does the carbon-carbon bond in pvc compare with that in chloroethene? A B C D longer longer shorter shorter stronger weaker stronger weaker 9701/1/M/J/02 [Turn over 8 23 2-Bromopropane, (CH3)2CHBr, may be used as the starting point for making (CH3)2CHCO2H. Which of the following sequences would be most suitable? A B C D (CH3)2CHBr → (CH3)2CHOH → (CH3)2CHCO2H (CH3)2CHBr → (CH3)2CHCN → (CH3)2CHCO2H (CH3)2CHBr → (CH3)2CHOH → (CH3)2CHCN → (CH3)2CHCO2H (CH3)2CHBr → (CH3)2CHCN → (CH3)2CHOH → (CH3)2CHCO2H 24 Which substance in a vehicle exhaust results from incomplete combustion of a hydrocarbon fuel? A CO B H2O C N2 D NO 25 Which compound on reaction with hydrogen cyanide produces a compound with a chiral centre? A B C D CH3CHO CH3CH2COCH2CH3 CH3CO2CH3 HCHO 26 An organic compound will decolorise dilute acidified aqueous potassium manganate(VII) on warming, but will not decolorise bromine water. What could the organic compound be? A B C D butane ethanol ethene ethanoic acid 27 A compound X has all of the following properties: it is a liquid at room temperature and atmospheric pressure; it does not mix completely with water; it does not decolorise acidified potassium manganate(VII). What could X be? A B C D ethane ethanoic acid ethanol ethyl ethanoate 9701/1/M/J/02 9 28 A compound R has all of the following properties: it is neutral; it gives an orange precipitate with 2,4-dinitrophenylhydrazine; it evolves hydrogen chloride when treated with PCl5 in the cold. What could R be? A COCH3 B OCH3 C O C CH2OH C O D CO2H CH3 29 MCPA and 2,4-D are two widely-used selective weedkillers. OCH2CO2H CH3 OCH2CH2OH Cl Cl MCPA Cl 2,4-D Which reagent will distinguish MCPA from 2,4-D? A B C D acidified AgNO3(aq) Fehling’s solution Na Na2CO3(aq) 9701/1/M/J/02 [Turn over 10 30 The acarid mite releases Iardolure to attract other mites to a host: this chemical can be destroyed by hydrolysis with acid. CH3CH2CH2[CH(CH3)CH2]3CH(CH3)O-C-H O A simplified formula for lardolure may be written as RCH(CH3)O-C-H. O What are the products of its hydrolysis? A B C D RCH(CH3)CO2H + CH3OH RCH(CH3)CO2H + HCO2H RCH(CH3)OH + CO2 RCH(CH3)OH + HCO2H 9701/1/M/J/02 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Which pairs of compounds have the same empirical formula? 1 2 3 ethane and ethene ethene and cyclohexane cyclohexane and oct-1-ene 32 In which sequences are the molecules quoted in order of increasing bond angle within the molecule? 1 2 3 H2O H2O CH4 NH3 SF6 CO2 CH4 BF3 SF6 33 The concepts of bond energy, bond length and bond polarity are useful when comparing the behaviour of similar molecules, e.g. thermal stability. For example, it could be said “Compared with the HCl molecule, the bond ……….X…………. of the HI molecule is ………..Y……….. .” Which pairs of words correctly complete the above sentence? X 1 2 3 energy length polarity Y greater greater less 9701/1/M/J/02 [Turn over 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 34 The equilibrium constant Kp for the reaction X(g) + Y(g) Z(g) varies with temperature as shown in the diagram below. Kp T Which conclusions can be drawn from this information? 1 2 3 The reaction is exothermic in the forward direction. The equilibrium mixture contains a greater proportion of Z at higher pressures. The equilibrium mixture contains a greater proportion of Z at higher temperatures. 35 When decomposing in water, organic refuse is oxidised to form carboxylic acids. The water becomes acidic and aquatic life is destroyed. Which additives are suitable to remove this acid pollution? 1 2 3 calcium carbonate calcium hydroxide potassium nitrate 36 Which properties would be expected for the Group II element, strontium, or its compounds? 1 2 3 When heated in oxygen, strontium does not burn. On being heated, strontium carbonate decomposes to give strontium oxide. When strontium oxide is added to water, the solution is alkaline. 9701/1/M/J/02 13 37 Which sodium salts form a precipitate when AgNO3(aq) followed by dilute NH3(aq) is added to its aqueous solution? 1 2 3 chloride bromide iodide 38 Which compounds would be formed in the reaction of ethene with aqueous bromine in the presence of sodium chloride? 1 2 3 CH2ClCH2Cl CH2BrCH2Cl CH2BrCH2Br 39 Halogenoalkanes react with aqueous alkali. One mechanism of this reaction has the reaction pathway diagram shown below. Z Y energy X R – Hal + OH– ROH + Hal– reaction pathway Which of the following statements are correct? 1 2 3 The reaction is an example of nucleophilic substitution. Between X and Y the C-Hal bond will be lengthening. The energy difference between X and Z represents the activation energy. 40 Which alcohols on oxidation with acidified potassium dichromate(VI) give an organic product which causes an effervescence when reacted with sodium carbonate? 1 2 3 butan-1-ol 2-methylpropan-1-ol 2-methylpropan-2-ol 9701/1/M/J/02 14 BLANK PAGE 9701/1/M/J/02 15 BLANK PAGE 9701/1/M/J/02 16 BLANK PAGE 9701/1/M/J/02 CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice 9701/01 May/June 2003 1 hour Additional Materials: Data Booklet Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers, A, B, C, and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 14 printed pages and 2 blank pages. SP (KN/KN) S34069/2 © CIE 2003 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 The use of the Data Booklet is relevant to this question. What is the number of molecules in 500 cm3 of oxygen under room conditions? A B C D 1.25 x 1022 1.34 x 1022 3.0 x 1022 3.0 x 1026 2 In the preparation of soft margarine, glyceryl trieleostearate CH3(CH2)3CH CH3(CH2)3CH CH3(CH2)3CH CHCH CHCH CHCH CHCH CHCH CHCH CH(CH2)7CO2CH2 CH(CH2)7CO2CH CH(CH2)7CO2CH2 is suitably hydrogenated so that, on average, one of its side-chains is converted into the CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2 residue and two side-chains are converted into the CH3(CH2)7CH=CH(CH2)7CO2 residue. How many moles of hydrogen are required to convert one mole of glyceryl trieleostearate into the soft margarine? A 4 B 5 C 6 D 9 3 Which isotope of an element in the third period of the Periodic Table contains the same number of 32 neutrons as 16 S? A B C D 23 11 Na 24 12 Mg 28 14 Si 31 15 P 4 The successive ionisation energies, in kJ mol–1, of an element X are given below. 870 1800 3000 3600 5800 7000 13 200 What is X? A 33As B 40Zr C 52Te D 9701/1/M/J/03 53I www.xtremepapers.net 3 5 Which of the following solids has a simple molecular lattice? A B C D magnesium oxide sodium silicon(IV) oxide sulphur 6 Measured values of the pressure, volume and temperature of a known mass of a gaseous compound are to be substituted into the equation pV = nRT in order to calculate the relative molecular mass, Mr, of the compound. Which conditions of pressure and temperature would give the most accurate value of Mr? pressure A B C D high high low low temperature high low high low 7 Gaseous phosphorus pentachloride can be decomposed into gaseous phosphorus trichloride and chlorine by heating. The table below gives the bond energies. bond P-Cl (in both chlorides) Cl-Cl bond energy / kJ mol–1 330 240 What is the enthalpy change in the decomposition of PCl5 to PCl3 and Cl2? A –420 kJ mol–1 B –90 kJ mol–1 C +90 kJ mol–1 D +420 kJ mol–1 9701/1/M/J/03 [Turn over www.xtremepapers.net 4 8 When ammonia is converted into nitric acid on a commercial scale, the following reactions can occur. In which reaction does the greatest change in oxidation number of the nitrogen occur? reaction A B C D 4NH3 + 5O2 → 4NO + 6H2O 3NO2 + H2O → 2HNO3 + NO 2NO + O2 → 2NO2 4NH3 + 6NO → 5N2 + 6H2O 9 At the age of 17, in a woodshed in Ohio, Charles Martin Hall discovered the commercial process for the production of aluminium metal by the electrolysis of a mixture of bauxite, Al2O3, and cryolite, Na3AlF6. What is the main purpose of the cryolite? A Al2O3 is covalent, and AlF 6 discharged at the cathode. 3– ions interact with it to produce Al 3+ ions which can be B C D Cryolite is a base, forming NaAlO2 with bauxite, enabling aluminium to be discharged at the anode. Cryolite reduces the melting point of the bauxite. Cryolite minimises the release of O2– ions at the graphite anodes, which are otherwise burnt away to CO. 10 When 0.20 mol of hydrogen gas and 0.15 mol of iodine gas are heated at 723 K until equilibrium is established, the equilibrium mixture is found to contain 0.26 mol of hydrogen iodide. The equation for the reaction is as follows. H2(g) + I2(g) 2HI(g) What is the correct expression for the equilibrium constant Kc? A B C D 2 x 0.26 ––––––––– 0.20 x 0.15 (2 x 0.26)2 ––––––––– 0.20 x 0.15 (0.26)2 ––––––––– 0.07 x 0.02 (0.26)2 ––––––––– 0.13 x 0.13 9701/1/M/J/03 www.xtremepapers.net 5 11 Why is ethanoic acid a stronger acid in liquid ammonia than in aqueous solution? A B C D Ammonia is a stronger base than water. Ammonium ethanoate is completely ionised in aqueous solution. Ammonium ethanoate is strongly acidic in aqueous solution. Liquid ammonia is a more polar solvent than water. 12 It is often said that the rate of a typical reaction is roughly doubled by raising the temperature by 10 °C. What explains this observation? A B C D Raising the temperature by 10 °C doubles the average energy of each molecule. Raising the temperature by 10 °C doubles the average velocity of the molecules. Raising the temperature by 10 °C doubles the number of molecular collisions in a given time. Raising the temperature by 10 °C doubles the number of molecules having more than a certain minimum energy. 13 A mixture of the oxides of two elements of the third period is dissolved in water. The solution is approximately neutral. What could be the constituents of the mixture? A B C D Al2O3 and MgO Na2O and MgO Na2O and P4O10 SO3 and P4O10 14 Aluminium chloride catalyses certain reactions by forming carbocations (carbonium ions) with chloroalkanes as shown. RCl + AlCl3 → R+ + AlCl – 4 Which property makes this reaction possible? A B C D AlCl3 is a covalent molecule. AlCl3 exists as the dimer Al2Cl6 in the vapour. The aluminium atom in AlCl 3 has an incomplete octet of electrons. The chlorine atom in RCl has a vacant p orbital. 9701/1/M/J/03 [Turn over www.xtremepapers.net 6 15 What are the products of the thermal decomposition of magnesium nitrate? A B C D magnesium nitride and oxygen magnesium oxide and nitrogen magnesium oxide, nitrogen and oxygen magnesium oxide, nitrogen dioxide and oxygen 16 Chlorine compounds show oxidation states ranging from –1 to +7. What are the reagent(s) and conditions necessary for the oxidation of elemental chlorine into a compound containing chlorine in the +5 oxidation state? A B C D AgNO3(aq) followed by NH3(aq) at room temperature concentrated H2SO4 at room temperature cold dilute NaOH(aq) hot concentrated NaOH(aq) 17 Which gaseous hydride most readily decomposes into its elements on contact with a hot glass rod? A B C D ammonia hydrogen chloride hydrogen iodide steam 18 Which reagent, when mixed and heated with ammonium sulphate, liberates ammonia? A B C D aqueous bromine dilute hydrochloric acid limewater acidified potassium dichromate(VI) 19 Which pollutant is formed in the internal combustion engine and, if not removed by the catalytic converter, may become involved in the formation of acid rain? A C B C8H18 C CO D NO 20 How many structural and cis-trans isomers are there for dichloropropene, C3H4Cl2? A 3 B 5 C 6 D 7 9701/1/M/J/03 www.xtremepapers.net 7 21 The isomers, citric acid and isocitric acid, are intermediates in the Krebs cycle of the oxidation of glucose in living cells. CH2CO2H C(OH)CO2H CH2CO2H citric acid How many chiral centres does each acid possess? citric acid A B C D 0 0 1 1 isocitric acid 1 2 1 2 CH2CO2H CHCO2H CH(OH)CO2H isocitric acid 22 The compound hex-3-en-1-ol, P, has a strong ‘leafy’ smell of newly cut grass and is used in perfumery. CH3CH2CH=CHCH2CH2OH P What is produced when P is treated with an excess of hot concentrated acidic KMnO4? A B C D CH3CH2CH(OH)CH(OH)CH2CH2OH CH3CH2CH=CHCH2CO2H CH3CH2CHO and OCHCH2CH2OH CH3CH2CO2H and HO2CCH2CO2H 9701/1/M/J/03 [Turn over www.xtremepapers.net 8 23 The complete combustion of alkanes to produce carbon dioxide and water is an important exothermic reaction. Which line on the graph shows the relationship between the number of carbon atoms in the alkane and the number of moles of oxygen gas needed for complete combustion of the alkane? A B number of moles of oxygen gas C D 1 number of carbon atoms in alkane 24 Cyclohexa-1,4–diene is treated with a solution of bromine in tetrachloromethane. cyclohexa-1,4-diene Which product is formed? A Br Br Br Br B Br Br C Br Br Br D Br Br Br 9701/1/M/J/03 Br Br www.xtremepapers.net 9 25 Which reaction is not an electrophilic addition? A B C D CH2=CH2 + HI → CH3CH2I CH3CH=CH2 + Br2 → CH3CHBrCH2Br 2 4 CH3CH=CH2 + H2O → CH3CH(OH)CH3 conc H SO CH3CHO + HCN → CH3CH(OH)CN 26 The reaction scheme outlines the production of one of the monomers of nylon 66 from compound X. KCN reduction H2N(CH2)6NH2 compound X NCCH2CH2CH2CH2CN in ethanol Which compound could be X? A B C D BrCH2CH2CH2CH2Br CH2=CHCH=CH2 HOCH2CH2CH2CH2OH HO2CCH2CH2CH2CH2CO2H 27 Chlorofluoroalkanes, commonly known as CFCs, undergo homolytic fission by ultraviolet irradiation in the stratosphere. Which radical could result from this irradiation of CHFClCF2Cl ? A B C D CHFCl CFCl · · · CHFCF2Cl · CFClCF Cl 2 CHClCF2Cl 28 In its reaction with sodium, 1 mol of a compound X gives 1 mol of H2(g). Which compound might X be? A B C D CH3CH2CH2CH2OH (CH3)3COH CH3CH2CH2CO2H CH3CH(OH)CO2H 9701/1/M/J/03 [Turn over www.xtremepapers.net 10 29 In a preparation of ethene, ethanol is added a drop at a time to a heated reagent Y. To purify the ethene it is bubbled through a solution Z and then collected. What could reagent Y and solution Z be? reagent Y A B C D acidified K2Cr2O7 concentrated H2SO4 concentrated H2SO4 ethanolic NaOH solution Z dilute NaOH dilute H2SO4 dilute NaOH concentrated H2SO4 30 The product of the reaction between propanone and hydrogen cyanide is hydrolysed under acidic conditions. What is the formula of the final product? A B C D CH3CH(OH)CO2H CH3CH2CH2CO2H (CH3)2CHCONH2 (CH3)2C(OH)CO2H 9701/1/M/J/03 www.xtremepapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Silicon tetrachloride, SiCl4, is a liquid of low boiling point. In the presence of water it decomposes to form silicon(IV) oxide and hydrogen chloride. What types of bonding occur in SiCl4(I)? 1 2 3 co–ordinate bonding covalent bonding van der Waals forces 32 Long-chain alkanes are converted on an industrial scale into alkylsulphates for use as detergents, e.g. sodium lauryl sulphate. O CH3(CH2)10CH2O S O sodium lauryl sulphate What deductions about the properties of this substance can be made from this structure? 1 2 3 Part of the structure is polar and is water–attracting. The alkyl chain is soluble in oil droplets. All the C-C-C bond angles are tetrahedral. ONa 9701/1/M/J/03 [Turn over www.xtremepapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 33 The conversion of graphite into diamond is an endothermic reaction (∆H = +3 kJ mol–1). C(graphite) → C(diamond) Which statements are correct? 1 2 3 The enthalpy change of atomisation of diamond is smaller than that of graphite. The bond energy of the C–C bonds in graphite is greater than that in diamond. The enthalpy change of combustion of diamond is greater than that of graphite. 34 Which of the following statements are correct for the sequence of compounds below considered from left to right? NaF 1 2 3 MgO Al N SiC The electronegativity difference between the elements in each compound increases. The formula-units of these compounds are isoelectronic (have the same number of electrons). The bonding becomes increasingly covalent. 35 Which statements are reasons why sulphur dioxide is used as a food preservative? 1 2 3 It is a reducing agent and therefore an anti-oxidant. It prevents alcohols forming sour-tasting acids. It does not smell and therefore can be used in more than trace quantities. 36 Why is the addition of concentrated sulphuric acid to solid potassium iodide unsuitable for the preparation of hydrogen iodide? 1 2 3 Hydrogen iodide is not displaced by sulphuric acid. Iodide ions are oxidised to iodine. The product is contaminated by sulphur compounds. 9701/1/M/J/03 www.xtremepapers.net 13 37 What will always be a characteristic of a compound containing a single carbon atom with four different groups bonded to it? 1 2 3 It will have an optical isomer. It will have a chiral centre. It will have a structural isomer. 38 Chloroethane can be formed from bromoethane in two steps. step X C2H5Br C2H5OH step Y C2H5Cl Which statements about these steps are correct? 1 2 3 Step X involves a nucleophilic substitution. Hot aqueous sodium hydroxide is the reagent in step X. Hot aqueous sodium chloride is the reagent in step Y. 39 When the apparatus below was used with compound Z, a brick-red precipitate formed in the righthand tube. air to pump Fehling's reagent compound Z in acidified potassium dichromate(VI) heat Which compound could be Z? 1 CH3CH(OH)CH3 2 CH3CH2CH2OH 3 CH3OH 9701/1/M/J/03 [Turn over www.xtremepapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 40 Mevalonic acid is an intermediate in the biosynthesis of cholesterol, and is shown below. OH HO2CCH2CCH2CH2OH CH3 Which properties does mevalonic acid have? 1 2 3 It has only one chiral carbon atom. It can be esterified both by ethanoic acid and by ethanol, in the presence of H+ ions. It contains both primary and secondary alcohol groups. 9701/1/M/J/03 www.xtremepapers.net 15 BLANK PAGE 9701/1/M/J/03 www.xtremepapers.net 16 BLANK PAGE 9701/1/M/J/03 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice May/June 2004 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C, and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read the instructions on the answer sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 13 printed pages and 3 blank pages. IB04 06_9701_01/3RP Ó UCLES 2004 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Which of these samples of gas contains the same number of atoms as 1g of hydrogen (Mr : H2, 2)? A B C D 2 22 g of carbon dioxide (Mr : CO2, 44) 8 g of methane (Mr : CH4, 16) 20 g of neon (Mr : Ne, 20) 8 g of ozone (Mr : O3, 48) Self-igniting flares contain Mg3P2. With water this produces diphosphane, P2H4, which is spontaneously flammable in air. Which equation that includes the formation of diphosphane is balanced? A B C D Mg3P2 + 6H2O ® 3Mg(OH)2 + P2H4 Mg3P2 + 6H2O ® 3Mg(OH)2 + P2H4 + H2 2Mg3P2 + 12H2O ® 6Mg(OH)2 + P2H4 + 2PH3 2Mg3P2 + 12H2O ® 6Mg(OH)2 + 3P2H4 3 Use of the Data Booklet is relevant to this question. Most modern cars are fitted with airbags. These work by decomposing sodium azide to liberate nitrogen gas, which inflates the bag. 2NaN3 ® 3N2 + 2Na A typical driver’s airbag contains 50 g of sodium azide. Calculate the volume of nitrogen this will produce at room temperature. A 9.2 dm3 B 13.9 dm3 C 27.7 dm3 D 72.0 dm3 4 What is the order of increasing energy of the listed orbitals in the atom of titanium? A B C D 3s 3p 3d 4s 3s 3p 4s 3d 3s 4s 3p 3d 4s 3s 3p 3d Ó UCLES 2004 9701/01/M/J/04 www.xtremepapers.net 3 5 Which of the following particles would, on losing an electron, have a half-filled set of p orbitals? A 6 C– B N C N– D O + Magnesium oxide is used to line industrial furnaces because it has a very high melting point. Which type of bond needs to be broken for magnesium oxide to melt? A B C D co-ordinate covalent ionic metallic 7 Which solid exhibits more than one kind of chemical bonding? A B C D brass copper diamond ice 8 The standard enthalpy changes of formation of iron(II) oxide, FeO(s), and aluminium oxide, Al2O3(s), are –266 kJ mol–1 and –1676 kJ mol–1 respectively. What is the enthalpy change under standard conditions for the following reaction? 3FeO(s) + 2Al (s) ® 3Fe(s) + Al 2O3(s) A + 878 kJ B – 878 kJ C –1942 kJ D –2474 kJ 9 Which substance, in 1 mol dm–3 aqueous solution, would have the same hydrogen ion concentration as 1 mol dm-3 of hydrochloric acid? A B C D ethanoic acid nitric acid sodium hydroxide sulphuric acid Ó UCLES 2004 9701/01/M/J/04 [Turn over www.xtremepapers.net 4 10 When vanadium(II) compounds are dissolved in water, the following equilibrium is established. V 2+ + H2O V 3+ + 1 H 2 + OH– 2 What would alter the composition of the equilibrium mixture in favour of the V 2+ ions? A B C D adding an acid adding a reagent that selectively precipitates V3+ ions allowing the hydrogen to escape as it forms making the solution more alkaline 11 In an industrial process, two gases X and Y react together to form a single gaseous product Z. X (g) + Y (g) Z (g) The percentage yield of product Z varies according to the pressure and the temperature as shown in the graphs. 100 90 80 70 equilibrium % of Z 60 50 40 30 20 10 0 25 100 200 300 400 pressure / atm 773 K 673 K 373 K 473 K 573 K Which statement about this equilibrium reaction is correct? A B C D Decreasing the temperature decreases the value of the equilibrium constant. Decreasing the temperature increases the rate of this reaction. Increasing the pressure increases the value of the equilibrium constant. The reaction is exothermic in the forward direction. Ó UCLES 2004 9701/01/M/J/04 www.xtremepapers.net 5 12 Four reactions of the type shown are studied at the same temperature. X (g) + Y (g) ® Z (g) Which is the correct reaction pathway diagram for the reaction that would proceed most rapidly and with good yield? A B energy energy reactant C product reactant D product energy energy reactant product reactant product 13 Which of these equations represents the reaction of sulphur dioxide with an excess of aqueous sodium hydroxide? A B C D SO2 + NaOH ® NaHSO3 SO2 + 2NaOH ® Na2SO3 + H2O SO2 + 2NaOH ® Na2SO4 + H2O SO2 + 2NaOH ® Na2SO4 + H2 14 Which ion is most polarising? A B C D Al 3+ Ba2+ Mg2+ Na+ Ó UCLES 2004 9701/01/M/J/04 [Turn over www.xtremepapers.net 6 15 Which element has the same oxidation number in all of its known compounds? A B C D beryllium chlorine nitrogen sulphur 16 Due to their similar ionic radii, the reactions of lithium and magnesium and their corresponding compounds are very similar. Which statement concerning the reactions of lithium and its compounds is correct? A B C D Lithium carbonate decomposes on heating at a relatively low temperature, forming lithium oxide and carbon dioxide. Lithium nitrate decomposes on heating, forming lithium nitrite and oxygen. Lithium only burns slowly in oxygen. Lithium reacts violently with cold water, liberating hydrogen. 17 Which statement is most likely to be true for astatine, which is below iodine in Group VII of the Periodic Table? A B C D Astatine and aqueous potassium chloride react to form aqueous potassium astatide and chlorine. Potassium astatide and hot dilute sulphuric acid react to form white fumes of only hydrogen astatide. Silver astatide reacts with dilute aqueous ammonia in excess to form a solution of a soluble complex. Sodium astatide and hot concentrated sulphuric acid react to form astatine. 18 Use of the Data Booklet is relevant to this question. In the commercial electrolysis of brine, the products are chlorine, hydrogen and sodium hydroxide. What is the maximum yield of each of these products when 58.5 kg of sodium chloride are electrolysed as brine? yield of chlorine / kg A B C D 35.5 35.5 71 71 yield of hydrogen / kg 1 2 1 2 yield of sodium hydroxide / kg 40 40 40 80 Ó UCLES 2004 9701/01/M/J/04 www.xtremepapers.net 7 19 Nitrogen dioxide and sulphur dioxide have some properties in common. Which property is shown by one of these compounds, but not by the other? A B C D forms ‘acid-rain’ is a reducing agent is insoluble in water is used as a food-preservative 20 Which molecule is planar? A B C D NF3 C2Cl 4 C3H6 C3H8 21 Which of these always applies to a nucleophile? A B C D It attacks a double bond. It has a lone pair of electrons. It is a single atom. It is negatively charged. 22 Compound P displays cis-trans isomerism and gives a red-brown precipitate with Fehling’s solution. What is P? A H C H C CH3 CH3 CH2CHO H C C H B COCH3 C H C H C CHO H CH3 CH3 C D H C CHO Ó UCLES 2004 9701/01/M/J/04 [Turn over www.xtremepapers.net 8 23 Which compound could not be obtained from cracking a sample of nonane, CH3(CH2)7CH3? A B C D CH3CH=CHCH=CHCH2CH2CH2CH3 CH3CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH=CH2 (CH3CH2CH2)3CH 24 In which way are ethene and propane similar? CH2=CH2 ethene A B C D CH3CH2CH3 propane They are both obtained by the dehydration of alcohols. They are both neutral to an indicator solution. They can both be hydrogenated using a suitable catalyst. They can both undergo polymerisation under suitable conditions. 25 Which reaction in the catalytic converter does not remove hazardous and polluting gases from the exhaust fumes of a motor car? gases going out gases going in: carbon monoxide, hydrocarbons and oxides of nitrogen surfaces coated with platinum and rhodium catalyst These equations are qualitative and unbalanced. [HC = unburnt hydrocarbons; NOx = oxides of nitrogen] A B C D HC + NOx ® H2O + CO + N2 CO + NOx ® CO2 + N2 HC + NOx ® H2O + CO2 + N2 CO + O2 ® CO2 Ó UCLES 2004 9701/01/M/J/04 www.xtremepapers.net 9 26 A possible mechanism of the hydrolysis of 2-chloro-2-methylpropane is shown. CH3 CH3 C CH3 Cl slow CH3 CH3 C+ + Cl CH3 _ CH3 CH3 C+ + CH3 OH _ CH3 fast CH3 C CH3 OH Which diagram represents the reaction profile for this mechanism? A B C D energy energy energy reaction path reaction path reaction path energy reaction path 27 Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH. Which statement is correct for these products? A B C D Both products are obtained in this reaction by electrophilic substitution. Both products are obtained in this reaction by nucleophilic addition. Both products can be hydrolysed to form the same diol. Both products can form hydrogen bonds with water. Ó UCLES 2004 9701/01/M/J/04 [Turn over www.xtremepapers.net 10 28 Compound X · · has the molecular formula C10H14O; is unreactive towards mild oxidising agents. What is the structure of the compound formed by dehydration of X? A CH2 CH2 CH CH2 CH2 B CH CH CH3 C CH3 CH CH CH2 D CH3 C CH CH3 29 For which pair of compounds can the members be distinguished by means of Tollens’ test (the + use of a solution containing Ag(NH3) 2 )? A B C D CH3CHO and CH3COCH3 CH3COCH3 and C2H5COCH3 CH3COCH3 and CH3CO2CH3 CH3CO2H and CH3CO2CH3 30 Compound X changes the colour of acidified sodium dichromate(VI) from orange to green. 1 mol of X reacts with 2 mol of HCN(g). What could X be? A B C D CH3COCH2COCH3 CH3CH2CH2CHO H2C=CHCH2CHO OHCCH2CH2CHO Ó UCLES 2004 9701/01/M/J/04 www.xtremepapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 The isotope cobalt-60 ( 60 Co ) is used to destroy cancer cells in the human body. 27 Which statements about an atom of cobalt-60 are correct? 1 2 3 It contains 33 neutrons. Its nucleus has a relative charge of 27+. It has a different number of neutrons from the atoms of other isotopes of cobalt. 32 The conversion of graphite has only a small positive value of DH. C (graphite) ® C (diamond) DH = +2.1 kJ mol –1 However, the production of synthetic diamonds using this reaction is very difficult. Which statements help to explain this? 1 2 3 The activation energy of the reaction is large. An equilibrium exists between diamond and graphite. Only exothermic reactions can be made to occur readily. 33 Which statements about the properties of a catalyst are correct? 1 2 3 A catalyst increases the average kinetic energy of the reacting particles. A catalyst increases the rate of the reverse reaction. A catalyst has no effect on the enthalpy change DH of the reaction. o Ó UCLES 2004 9701/01/M/J/04 [Turn over www.xtremepapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 34 Which pairs of compounds contain one that is giant ionic and one that is simple molecular? 1 Al 2O3 and Al 2Cl 6 2 SiO2 and SiCl 4 3 P4O10 and PCl 3 35 When coal is burnt, gaseous oxides of carbon and sulphur are formed which pollute the atmosphere. One method of preventing such pollution involves adding calcium carbonate to the burning coal. The temperature of the process causes the decomposition of the calcium carbonate into calcium oxide. Which reactions will be important in helping to reduce atmospheric pollution? 1 2 3 Calcium oxide reacts with sulphur dioxide to form calcium sulphite. Calcium oxide reacts with sulphur dioxide and more air to form calcium sulphate. Calcium oxide reacts with carbon monoxide to form calcium carbonate. 36 When a hot glass rod is placed in a gas jar of hydrogen iodide, there is an immediate reaction as the hydrogen iodide decomposes. Which statements about this reaction are correct? 1 2 3 Hydrogen iodide is purple coloured. The hot rod provides the activation energy. One of the products is a solid. Ó UCLES 2004 9701/01/M/J/04 www.xtremepapers.net 13 37 Acrolein is produced in photochemical smog. It has a strong smell, irritates eyes and mucous membranes and is carcinogenic. H C C H H acrolein C O H What can be deduced from this structure? 1 2 3 All bond angles are approximately 120 o. It will undergo electrophilic addition reactions. It will undergo nucleophilic addition reactions. 38 What can be produced when an aqueous solution of butan-1-ol is heated with dilute acidified potassium manganate(VII)? 1 2 3 butanal butanoic acid butanone 39 Which carbonyl compounds could be easily oxidised to carboxylic acids that are readily soluble in cold water? 1 CH3CH2CHO 2 3 CHO CO 40 Which properties of poly(alkenes) and of pvc can cause their disposal to be difficult? 1 2 3 Poly(alkenes) are highly flammable. Poly(alkenes) are non–biodegradable. pvc produces harmful combustion products. Ó UCLES 2004 9701/01/M/J/04 www.xtremepapers.net 14 BLANK PAGE 9701/01/M/J/04 www.xtremepapers.net 15 BLANK PAGE 9701/01/M/J/04 www.xtremepapers.net 16 BLANK PAGE University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES) which is itself a department of the University of Cambridge. 9701/01/M/J/04 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice May/June 2005 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read the instructions on the answer sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. You may use a calculator. This document consists of 15 printed pages and 1 blank page. IB05 06_9701_01/3RP  UCLES 2005 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 A pure hydrocarbon is used in bottled gas for cooking and heating. When 10 cm3 of the hydrocarbon is burned in 70 cm3 of oxygen (an excess), the final gaseous mixture contains 30 cm3 of carbon dioxide and 20 cm3 of unreacted oxygen. All gaseous volumes were measured under identical conditions. What is the formula of the hydrocarbon? A C2H6 B C3H6 C C3H8 D C4H10 2 On collision, airbags in cars inflate rapidly due to the production of nitrogen. The nitrogen is formed according to the following equations. 2NaN3 → 2Na + 3N2 10Na + 2KNO3 → K2O + 5Na2O + N2 How many moles of nitrogen gas are produced from 1 mol of sodium azide, NaN3? A 1.5 B 1.6 C 3.2 D 4.0 3 The first six ionisation energies of four elements, A to D, are given. Which element is most likely to be in Group IV of the Periodic Table? ionisation energy / kJ mol−1 A B C D 1st 494 736 1090 1400 2nd 4560 1450 2350 2860 3rd 6940 7740 4610 4590 4th 9540 10500 6220 7480 5th 13400 13600 37800 9400 6th 16600 18000 47000 53200 4 In which species are the numbers of electrons and neutrons equal? A 9 4 Be B 19 9F C 23 + 11 Na D 18 2– 8O © UCLES 2005 9701/01/M/J/05 www.xtremepapers.net 3 5 The diagram shows the variation of the boiling points of the hydrogen halides. b.p. HF HCl HBr HI What explains the higher boiling point of hydrogen fluoride? A B C D The bond energy of HF molecules is greater than in other hydrogen halides. The effect of nuclear shielding is much reduced in fluorine which polarises the HF molecule. The electronegativity of fluorine is much higher than for other elements in the group. There is hydrogen bonding between HF molecules. 6 Three substances, R, S, T, have physical properties as shown. electrical conductivity substance R S T mp / oC 801 2852 3550 bp / oC of solid 1413 3600 4827 poor poor good of liquid good good not known What could be the identities of R, S and T ? R A B C D NaF NaBr NaCl NaBr S KCl BaO MgO CaO T Cu SiO2 C [graphite] C [diamond] © UCLES 2005 9701/01/M/J/05 [Turn over www.xtremepapers.net 4 7 Iodine trichloride, ICl3, is made by reacting iodine with chlorine. I2(s) + Cl2(g) → 2ICl(s) ; ∆H o = +14 kJ mol–1 ICl(s) + Cl2(g) → ICl3(s) ; ∆H o = –88 kJ mol–1 By using the data above, what is the enthalpy change of the formation for solid iodine trichloride? A B C D –60 kJ mol–1 –74 kJ mol–1 –81 kJ mol–1 –162 kJ mol–1 8 In the extraction of aluminium by electrolysis, why is it necessary to dissolve aluminium oxide in molten cryolite? A B C D to reduce the very high melting point of the electrolyte cryolite provides the ions needed to carry the current cryolite reacts with the aluminium oxide to form ions molten aluminium oxide alone would not conduct electricity 9 A cheap carbon monoxide detector for a gas heater consists of a patch containing palladium chloride crystals. When carbon monoxide is present, the crystals turn from orange to black as the following reaction takes place. CO(g) + PdCl2(s) + H2O(l) → CO2(g) + Pd(s) + 2HCl(aq) orange black Which is the element whose oxidation number decreases in this reaction? A B C D carbon chlorine hydrogen palladium © UCLES 2005 9701/01/M/J/05 www.xtremepapers.net 5 10 The dissociation of dinitrogen tetraoxide into nitrogen dioxide is represented by the equation below. N2O4(g) 2NO2(g); ∆H o = +57 kJ mol –1 If the temperature of an equilibrium mixture of the gases is increased at constant pressure, will the volume of the mixture increase or decrease and why? A B C D The volume will increase, but only because of a shift of equilibrium towards the right. The volume will increase, both because of a shift of equilibrium towards the right and also because of thermal expansion. The volume will stay the same, because any thermal expansion could be exactly counteracted by a shift of equilibrium towards the left. The volume will decrease, because a shift of equilibrium towards the left would more than counteract any thermal expansion. 11 The reaction represented by the following equation was carried out. HCO2CH3(aq) + NaOH(aq) → HCO2Na(aq) + CH3OH(aq) Which graph best shows the relationship between [CH3OH(aq)] and t, the time from mixing of the reactants? A [CH3OH(aq)] [CH3OH(aq)] B 0 0 C [CH3OH(aq)] t 0 0 D [CH3OH(aq)] t 0 0 t 0 0 t © UCLES 2005 9701/01/M/J/05 [Turn over www.xtremepapers.net 6 12 The following species contain the same number of electrons. In which order do their radii increase? smallest radius A B C D Ar Ca2+ Ca2+ K+ K+ Ar K+ Ar largest radius Ca2+ K+ Ar Ca2+ 13 Use of the Data Booklet is relevant to this question. Which element is likely to have an electronegativity similar to that of aluminium? A B C D barium beryllium magnesium strontium 14 Use of the Data Booklet is relevant to this question. Which is true for calcium or its compounds compared with the corresponding statements for magnesium? A B C D Calcium has a smaller atomic radius. Calcium oxide reacts less vigorously with water. Calcium reacts more vigorously with water. The sum of the first two ionisation energies of calcium is greater. 15 Concentrated sulphuric acid is added to separate solid samples of sodium chloride, sodium bromide or sodium iodide. With which sample(s) does sulphuric acid act as an oxidising agent? A B C D sodium chloride only sodium chloride and sodium bromide sodium bromide and sodium iodide sodium iodide only © UCLES 2005 9701/01/M/J/05 www.xtremepapers.net 7 16 Which graph correctly describes a trend found in the halogen group? A bond length in X2 Cl2 Br2 I2 strength of van der Waals' forces Cl2 B Br2 I2 C boiling point of X2 Cl2 Br2 I2 bond energy of HX D H-Cl H-Br H-I 17 Limestone, CaCO3, has been used as a building material for thousands of years, and was used on the Pyramids in Egypt. In the past hundred years many limestone buildings have begun to suffer damage. What is the cause of this damage? A B C D hydrocarbon emissions from motor vehicles increased temperature due to global warming increased ultraviolet radiation as the ozone layer is destroyed sulphur dioxide from fossil fuels forming ‘acid rain’ 18 In an historically famous experiment Wöhler heated “inorganic” ammonium cyanate in the absence of air. The only product of the reaction was “organic” urea, CO(NH2)2. No other products were formed in the reaction. What is the formula of the cyanate ion present in ammonium cyanate? A CNO– B CNO2– C CO– D NO– © UCLES 2005 9701/01/M/J/05 [Turn over www.xtremepapers.net 8 19 Bromomethane, CH3Br, is used as a fumigant to destroy insect pests in grain that is to be stored. It can be made by reacting methanol with hydrogen bromide. CH3OH + HBr → CH3Br + H2O What type of reaction is this? A B C D condensation electrophilic substitution free radical substitution nucleophilic substitution 20 Prop-2-en-1-ol (allyl alcohol) has the following structure. H H C H H C C OH H Which reagent would react with prop-2-en-1-ol to form a product that could exist as optical isomers? A B C D bromine hydrogen and nickel phosphorus pentachloride sodium 21 Under the Montreal Protocol the use of chlorofluorocarbons is to be phased out. Fluorocarbons are often used to replace them. One chlorofluorocarbon which was widely used as a solvent is CCl2FCCl F2 and large stocks of it remain. One process to use up these stocks is to convert it into the fluorocarbon CH2FCF3 by the following route. step 1 CCl2FCCl F2 What type of reaction is step 1? A B C D elimination free radical substitution isomerisation nucleophilic substitution step 2 CCl3CF3 CCl2FCF3 step 3 CH2FCF3 © UCLES 2005 9701/01/M/J/05 www.xtremepapers.net 9 22 When bromine reacts with propene in an organic solvent at room temperature, what is the mechanism by which the bromine attacks the propene? A B C D electrophilic addition electrophilic substitution nucleophilic addition nucleophilic substitution 23 Dichlorodifluoromethane, CCl2F2, has been used in aerosol propellants and as a refrigerant. Which statement helps to explain why dichlorodifluoromethane is chemically inert? A B C D The carbon-fluorine bond energy is large. The carbon-fluorine bond has a low polarity. Fluorine is highly electronegative. Fluorine compounds are non-flammable. 24 Under identical conditions, even though it proceeds by the same mechanism, reaction 1 is faster than reaction 2. reaction 1 reaction 2 CH3CHBrCH3 + NaCN → CH3CH(CN)CH3 + NaBr CH3CHBrCH3 + NaI → CH3CHICH3 + NaBr What factor will explain this result? A B C D The C The C I bond is a stronger bond than the C N bond is a stronger bond than the C Br bond. I bond. The cyanide ion is a stronger nucleophile than the iodide ion. The cyanide ion is a weaker nucleophile than the iodide ion. © UCLES 2005 9701/01/M/J/05 [Turn over www.xtremepapers.net 10 25 Ethyl ethanoate is a very important solvent in industry. Currently, researchers are investigating ways of producing the ester from cheap, low grade ethanol by the following process. step 1 CH3CH2OH CH3CHO step 2 CH3CH2OCHCH3 OH step 3 CH3CH2OCOCH3 What types of reaction are steps 1 and 3? step 1 A B C D elimination elimination oxidation oxidation step 3 esterification isomerisation esterification oxidation 26 Malic acid occurs in apples. OH H C CO2H malic acid CH2CO2H Which substance will react with all three –OH groups present in the malic acid molecule? A B C D ethanol in the presence of concentrated sulphuric acid potassium hydroxide sodium sodium carbonate 27 Which compound reacts with its own oxidation product (an oxidation which involves no loss of carbon) to give a sweet-smelling liquid? A B C D propanal propanoic acid propanone propan–1–ol © UCLES 2005 9701/01/M/J/05 www.xtremepapers.net 11 28 Which reagent could be used to distinguish between CH3CH(OH)CH2CHO and CH3COCH2CH2OH ? A B C D acidified potassium dichromate(VI) dilute sulphuric acid 2,4–dinitrophenylhydrazine Fehling’s reagent 29 Ibuprofen is an anti-inflammatory drug. (CH3)2CHCH2 ibuprofen CH(CH3)CO2H What reaction would lead to its formation? CH3 A (CH3)2CHCH2 C CH2 B (CH3)2CHCH2 CH(CH3)CHO + warm acidified K2Cr2O7 + hot concentrated KMnO4 C (CH3)2CHCH2 CH(CH3)COCH3 + warm H2SO4(aq) D CH2=C(CH3)CH2 CCOCH3 CH2 + H2 / Pt catalyst 30 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated? A B C D It can be melted down and re-used. Its combustion products are harmful. It destroys the ozone layer. It does not burn easily. © UCLES 2005 9701/01/M/J/05 [Turn over www.xtremepapers.net 12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Which of the following molecules and ions have a regular trigonal planar shape? 1 2 3 Al Cl3 CH3 PH3 + 32 A quantity of solid Y was placed in a previously evacuated vessel and the apparatus was then held at a series of different temperatures. At each temperature, the mass of Y in the vapour state was calculated from pressure measurements. The results are shown below. mass of vapour m T temperature What can be deduced from the diagram? 1 2 3 The mass of Y used in the experiment was m. The pressure of the vapour was constant for all temperatures above temperature T. Liquid appeared at temperature T. © UCLES 2005 9701/01/M/J/05 www.xtremepapers.net 13 33 Which of the enthalpy changes of the following reactions can only be obtained by application of Hess’ Law? 1 2 3 The hydration of anhydrous copper sulphate to form crystals of CuSO4.5H2O. The formation of methane from its elements. The combustion of glucose, C6H12O6. 34 The stoichiometry of a catalysed reaction is shown by the equation below. P (g) + Q (g) R (g) + S (g) Two experiments were carried out in which the production of R was measured against time. The results are shown in the diagram below. experiment 1 amount of R experiment 2 0 0 time Which changes in the conditions from experiment 1 to experiment 2 might explain the results shown? 1 2 3 Less of P was used. A different catalyst was used. Product S was continuously removed from the reaction vessel. 35 Use of the Data Booklet is relevant to this question. Which properties would be expected from radium, 88Ra, or its compounds? 1 2 3 Radium carbonate decomposes only at a very high temperature. Radium hydroxide is very insoluble. Radium does not react with cold water. © UCLES 2005 9701/01/M/J/05 [Turn over www.xtremepapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 36 The number of moles of chlorine that react with 1 mol of X is twice the number of moles of chlorine that react with 1 mol of Y. Which of these pairs could be X and Y? X 1 2 3 Mg(s) H2 cold NaOH(aq) Y Na(s) KBr(aq) hot NaOH(aq) 37 Which statements are true about the Haber process for the manufacture of ammonia? 1 2 3 At higher temperatures, the yield goes down but the rate of production of ammonia is faster. At higher pressures, the yield goes down but the rate of production of ammonia is faster. In the presence of a catalyst, the yield goes down but the rate of production of ammonia is faster. 38 Which compounds can be obtained from ethene in a single reaction? 1 2 3 CH3CH3 ( CH2CH2 ) n HOCH2CH2OH © UCLES 2005 9701/01/M/J/05 www.xtremepapers.net 15 39 The steroid shown is an intermediate compound obtained during the synthesis of Formestane which is used in the treatment of breast cancer. CH3 O CH3 HO OH Which statements about this compound are correct? 1 2 3 It reacts with hydrogen cyanide in a nucleophilic addition reaction. It can be oxidised by warm acidified potassium dichromate(VI) to a carboxylic acid. It will react with Fehling’s solution. 40 A sun protection cream contains the following ester as its active ingredient. CH2CH2 CH2CH2CH2CH3 CH3O CH CHCO2CH2CH What are the products of its partial or total hydrolysis by aqueous sodium hydroxide? 1 CH3CH2CH2CH2CH(CH2CH3)CH2OH CH3O CH3O CH CHCO2 Na+ CO- Na+ 2 2 3 © UCLES 2005 9701/01/M/J/05 www.xtremepapers.net 16 BLANK PAGE Every reasonable effort has been made to trace all copyright holders where the publishers (i.e. UCLES) are aware that third-party material has been reproduced. The publishers would be pleased to hear from anyone whose rights they have unwittingly infringed. University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. 9701/01/M/J/05 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice May/June 2006 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 14 printed pages and 2 blank pages. IB06 06_9701_01/3RP  UCLES 2006 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 N2O4 is a poisonous gas. It can be disposed of safely by reaction with sodium hydroxide. N2O4(g) + 2NaOH(aq) → NaNO3(aq) + NaNO2(aq) + H2O(l) What is the minimum volume of 0.5 mol dm–3 NaOH(aq) needed to dispose of 0.02 mol of N2O4? A 2 8 cm3 B 12.5 cm3 C 40 cm3 D 80 cm3 A sample of chlorine containing isotopes of mass numbers 35 and 37 was analysed in a mass-spectrometer. + How many peaks corresponding to Cl 2 were recorded? A 3 2 B 3 C 4 D 5 Gallium nitride, GaN, could revolutionise the design of electric light bulbs because only a small length used as a filament gives excellent light at low cost. Gallium nitride is an ionic compound containing the Ga3+ ion. What is the electron arrangement of the nitrogen ion in gallium nitride? A B C D 1s2 2s2 1s2 2s2 2p3 1s2 2s2 2p4 1s2 2s2 2p6 201 81 4 A radioactive isotope of thallium, attack. Which statement about A B C D 201 81 Tl, is used to assess damage in heart muscles after a heart Tl is correct? This isotope has a nucleon number of 120. The number of electrons in one atom of this isotope is 81. The number of neutrons in one atom of this isotope is 201. 201 82 X is an isotope of 201 81 Tl. © UCLES 2006 9701/01/M/J/06 www.xtremepapers.net 3 5 In which process are hydrogen bonds broken? A B C D 6 H2(l) → H2(g) NH3(l) → NH3(g) 2HI(g) → H2(g) + I2(g) CH4(g) → C(g) + 4H(g) Which of the following least resembles an ideal gas? A B C D ammonia helium hydrogen trichloromethane represent 7 The diagram shows part of the lattice structures of solids X and Y. [In X, particles of different elements.] X Y What are the types of bonding present in X and Y? X A B C D covalent ionic ionic metallic Y metallic covalent metallic ionic © UCLES 2006 9701/01/M/J/06 [Turn over www.xtremepapers.net 4 8 In the conversion of compound X into compound Z, it was found that the reaction proceeded by way of compound Y, which could be isolated. The following steps were involved. X → Y ; ∆H, positive Y → Z ; ∆H, negative Which reaction profile fits these data? A B Y C D energy energy energy energy Y X progress of reaction Y Z X progress of reaction X Y progress of reaction Z X Z progress of reaction Z 9 The nickel-cadmium rechargeable battery is based upon the following overall reaction. Cd + 2NiOOH + 4H2O → Cd(OH)2 + 2Ni(OH)2.H2O What is the oxidation number of nickel at the beginning and at the end of the reaction? beginning A B C D +1.5 +2 +3 +3 end +2 +3 +2 +4 10 At a total pressure of 1.0 atm, dinitrogen tetraoxide is 50 % dissociated at a temperature of 60 oC, according to the following equation. N2O4 2NO2 What is the value of the equilibrium constant, Kp, for this reaction at 60 oC? A 1 /3 atm B 2 /3 atm C 4 /3 atm D 2 atm © UCLES 2006 9701/01/M/J/06 www.xtremepapers.net 5 11 Swimming pool water can be kept free of harmful bacteria by adding aqueous sodium chlorate(I), NaOCl. This reacts with water to produce HOCl molecules which kill bacteria. OCl –(aq) + H2O OH–(aq) + HOCl (aq) In bright sunshine, the OCl – ion is broken down by ultra-violet light. OCl –(aq) + uv light → Cl –(aq) + ½O2(g) Which method would maintain the highest concentration of HOCl (aq)? A B C D acidify the pool water add a solution of chloride ions add a solution of hydroxide ions bubble air through the water 12 Which solid-line curve most accurately represents the distribution of molecular speeds in a gas at 500 K if the dotted-line curve represents the corresponding distribution for the same gas at 300 K? A fraction of molecules fraction of molecules B speed speed C fraction of molecules fraction of molecules D speed speed 13 In which pair is the radius of the second atom greater than that of the first atom? A Na, Mg B Sr, Ca C P, N D Cl, Br © UCLES 2006 9701/01/M/J/06 [Turn over www.xtremepapers.net 6 14 The oxide and chloride of an element X are separately mixed with water. The two resulting solutions have the same effect on litmus. What is element X? A B C D sodium magnesium aluminium phosphorus 15 Aluminium chloride sublimes at 178 oC. Which structure best represents the species in the vapour at this temperature? A Cl Al Cl Cl Cl Al Cl Cl Cl Cl Al Cl B Cl Al Cl Cl C Al + 3Cl D Al 3+(Cl –)3 16 Use of the Data Booklet is relevant to this question. What mass of solid residue can be obtained from the thermal decomposition of 4.10 g of anhydrous calcium nitrate? A 0.70 g B 1.00 g C 1.40 g D 2.25 g 17 What happens when chlorine is bubbled through aqueous potassium iodide? A B C D Chlorine is oxidised to chloride ions. Hydrochloric acid is formed. Iodide ions are oxidised to iodine. Potassium iodide is reduced to iodine. 18 The emissions from a power station contain about 14 tonnes of SO2 per hour from the oxidation of FeS2 contained in the coal. What is the most practical way of preventing the SO2 from being released into the atmosphere? A B C D Cool the gases and the SO2 will liquefy and can be removed. Dissolve the ionic FeS2 in hexane. Pass the emissions through a bed of calcium oxide. Pass the gases through concentrated sulphuric acid to dissolve the SO2. © UCLES 2006 9701/01/M/J/06 www.xtremepapers.net 7 19 The gaseous oxides of nitrogen have positive enthalpy changes of formation. Which factor is likely to make the most significant contribution to these enthalpy changes? A B C D the high bond energy of the nitrogen molecule, N2 the high electron affinity of nitrogen atoms the high electron affinity of oxygen atoms the similarity of the electronegativities of oxygen and nitrogen 20 A new industrial preparation of ethyl ethanoate has been developed using cheap sources of ethanol. Cu catalyst CH3CH2OH – H2 CH3CHO Cu catalyst + CH3CH2OH CH3CH(OH)OCH2CH3 Cu catalyst – H2 CH3CO2CH2CH3 Which process is involved at some stage in this reaction sequence? A B C D disproportionation electrophilic addition nucleophilic addition reduction 21 Warfarin is used as a rat poison. O O C C CH CH2 C O CH3 C OH warfarin How many chiral centres are present in the warfarin molecule? A 0 B 1 C 2 D 3 © UCLES 2006 9701/01/M/J/06 [Turn over www.xtremepapers.net 8 22 The structures below show isomers of C6H12. 1 CH3 C H C C 2H 5 H CH3 CH3 C 2 C2H 5 C CH3 C 2H 5 C CH3 3 H C CH3 H C 2H 5 C 4 CH3 C CH3 In which pair are the members cis-trans isomers of each other? A 1 and 2 B 1 and 3 C 1 and 4 D 2 and 4 23 Use of the Data Booklet is relevant to this question. In which reaction is the relative molecular mass of the organic product the largest? A B C D bromoethane + aqueous sodium hydroxide bromoethane + alcoholic sodium hydroxide ethane + bromine ethanol + phosphorus pentachloride 24 Light initiates the following reaction. alkane + chlorine → chloroalkane + hydrogen chloride What happens to chlorine in this photochemical reaction? A B C D heterolytic fission to give an electrophile homolytic fission to give an electrophile heterolytic fission to give a free radical homolytic fission to give a free radical 25 High-energy irradiation in the stratosphere produces radicals from chlorofluoroalkanes, commonly known as CFCs. Which radical could result from this irradiation of CHFClCF2Cl? A B C D CHFClCFCl CHClCF2Cl CHFCF2Cl CFClCF2Cl © UCLES 2006 9701/01/M/J/06 www.xtremepapers.net 9 26 Which reagent could detect the presence of alcohol in a petrol consisting mainly of a mixture of alkanes and alkenes? A B C D Na Br2 (in CCl4) KMnO4(aq) 2,4-dinitrophenylhydrazine 27 Which alcohol may be oxidised to a product which reacts with 2,4-dinitrophenylhydrazine reagent but not with Fehling’s reagent? A B C D butan-1-ol butan-2-ol 2-methylpropan-1-ol 2-methylpropan-2-ol 28 The first stage in the synthesis of antipyrine, a drug used in reducing fever, is the reaction between compound P and phenylhydrazine. CH3COCH2CO2CH2CH3 P + NHNH2 phenylhydrazine Q What is the product Q of this first stage? A CH3COCH2CONH B NHCH2CO2CH2CH3 C CH3COCH2CO NHNH2 D NHN CH3CCH2CO2CH2CH3 © UCLES 2006 9701/01/M/J/06 [Turn over www.xtremepapers.net 10 29 Aldehydes and ketones are carbonyl compounds. Which of them react both with NaBH4 and with Tollens’ reagent? A B C D both aldehydes and ketones aldehydes only ketones only neither aldehydes nor ketones 30 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D − C3H7CO 2 Na + © UCLES 2006 9701/01/M/J/06 www.xtremepapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 The Group IV elements carbon, silicon and germanium all exist in a diamond structure. The bond lengths in these structures are given below. element X bond length X–X / nm C 0.154 Si 0.234 Ge 0.244 Why does the bond length increase down the group? 1 2 3 Orbital overlap decreases down the group. Atomic radius increases down the group. Nuclear charge increases down the group. 32 Sodium ions can be formed from sodium atoms. Na(s) → Na+(g) Which quantities are required to calculate the enthalpy change of formation of gaseous sodium ions? 1 2 3 enthalpy change of atomisation of sodium first ionisation energy of sodium enthalpy change of formation of sodium © UCLES 2006 9701/01/M/J/06 [Turn over www.xtremepapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 33 Hydrazine, N2H4, is widely used as a rocket fuel because it reacts with oxygen as shown, producing ‘environmentally friendly’ gases. N2H4(l) + O2(g) → N2(g) + 2H2O(g) ∆H = –534 kJ mol–1 Despite its use as a rocket fuel, hydrazine does not spontaneously burn in oxygen. Why does hydrazine not burn spontaneously? 1 The activation energy is too high. 2 The N≡N bond is very strong. 3 Hydrazine is a liquid. 34 Compound X • does not conduct electricity when in a liquid state, • when added to water produces a solution that readily conducts electricity. What could X be? 1 MgCl2 2 SiCl4 3 PCl3 © UCLES 2006 9701/01/M/J/06 www.xtremepapers.net 13 35 Hydroxyapatite, a basic calcium phosphate, Ca(OH)2.3Ca3(PO4)2, is the mineral found in bone. In older people, calcium ions can be lost from the hydroxyapatite, weakening the bone structure. In such cases, strontium salts are administered to strengthen the bone. The strontium ions replace the lost calcium ions in the hydroxyapatite. Which statements are correct? 1 2 3 Strontium ions are nearly the same size as calcium ions and so may easily replace them in the hydroxyapatite. Strontium hydroxide is less soluble than calcium hydroxide and so will precipitate better in the bone structure. There is ionic, covalent and metallic bonding in hydroxyapatite which gives it strength. 36 Ammonia and chlorine react in the gas phase. 8NH3 + 3Cl2 → N2 + 6NH4Cl Which statements are correct? 1 2 3 Ammonia behaves as a reducing agent. Ammonia behaves as a base. The oxidation number of the hydrogen changes. 37 In which pairs are the members stereoisomers of each other? 1 CH3 C Br H Cl Br C H H Cl Br C CH3 C Br H CH3 C H 2 CH3 C H 3 CH3 C H C Br CH3 C C H Cl Br Cl © UCLES 2006 9701/01/M/J/06 [Turn over www.xtremepapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 38 Deuterium, D, is the 2 H isotope of hydrogen. DBr has the same chemical properties as HBr. 1 Which compounds could be made by the reaction of DBr with another compound in a single reaction? Br D 1 2 CHBr2CHDBr OD 3 CH3CH Br 39 How can the rate of reaction between ethanal and aqueous hydrogen cyanide be increased? 1 2 3 by irradiation with ultraviolet light by a rise in temperature by the addition of a small quantity of aqueous sodium cyanide 40 Which statements about lactic acid, CH3CH(OH)CO2H, are correct? 1 2 3 Lactic acid forms optical isomers. Two hydrogen atoms per lactic acid molecule can be involved in hydrogen bonding. Lactic acid would form an aldehyde when oxidised by acidified potassium dichromate(VI). © UCLES 2006 9701/01/M/J/06 www.xtremepapers.net 15 BLANK PAGE 9701/01/M/J/06 www.xtremepapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. 9701/01/M/J/06 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 May/June 2007 1 hour *1603311060* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 14 printed pages and 2 blank pages. IB07 06_9701_01/3RP © UCLES 2007 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 The isotopic composition of an element is indicated below. 5 4 relative 3 abundance 2 1 0 9 10 11 12 mass number What is the relative atomic mass of the element? A 2 10.2 B 10.5 C 10.8 D 11.0 Use of the Data Booklet is relevant to this question. Oxides of nitrogen are pollutant gases which are emitted from car exhausts. In urban traffic, when a car travels one kilometre, it releases 0.23 g of an oxide of nitrogen NxOy, which occupies 120 cm3. What are the values of x and y? (Assume 1 mol of gas molecules occupies 24.0 dm3.) A B C D x = 1, y = 1 x = 1, y = 2 x = 2, y = 1 x = 2, y = 4 3 John Dalton’s atomic theory, published in 1808, contained four predictions about atoms. Which of his predictions is still considered to be correct? A B C D Atoms are very small in size. No atom can be split into simpler parts. All the atoms of a particular element have the same mass. All the atoms of one element are different in mass from all the atoms of other elements. © UCLES 2007 9701/01/M/J/07 www.xtremepapers.net 3 4 The diagrams show the possible paths of subatomic particles moving in an electric field in a vacuum. + electrons neutrons + protons + – 1 2 – 3 – Which diagrams are correct? A B C D 5 1 and 2 only 1 and 3 only 2 and 3 only 1, 2 and 3 The CN– ion is widely used in the synthesis of organic compounds. What is the pattern of electron pairs in this ion? bonding pairs of electrons A B C D 2 2 3 3 lone pairs on carbon atom 1 2 1 1 lone pairs on nitrogen atom 1 1 1 2 6 Plastic bottles for ‘fizzy drinks’ are made from a polymer with the following structure. H C C H H n X The ability of the polymer to prevent escape of carbon dioxide through the wall of the bottle depends on the ability of the group X to form hydrogen bonds with the carbon dioxide in the drink. Which group X best prevents loss of carbon dioxide? A Cl B CN C CO2CH3 D OH © UCLES 2007 9701/01/M/J/07 [Turn over www.xtremepapers.net 4 7 An exothermic chemical reaction proceeds by two stages. stage 1 reactants intermediate stage 2 products The activation energy of stage 1 is 50 kJ mol–1. The overall enthalpy change of reaction is –100 kJ mol–1. Which diagram represents the reaction pathway for this reaction? A 100 75 50 25 0 -25 reactants -50 -75 -100 products progress of reaction 8 B 100 75 50 25 0 -25 reactants -50 products -75 -100 progress of reaction C 100 75 50 25 0 -25 reactants -50 -75 products -100 progress of reaction D 100 75 50 25 0 -25 reactants -50 products -75 -100 progress of reaction Skiers trapped by snowstorms use heat packs to keep warm. The heat may be generated by the reaction below. 4Fe(s) + 3O2(g) → 2Fe2O3(s) ; ∆HO = –1648 kJ What is the standard enthalpy change of formation of iron(III) oxide? A B C D 9 0 kJ mol–1 –824 kJ mol–1 –1648 kJ mol–1 –3296 kJ mol–1 Two equilibria are shown below. reaction I reaction II 2X2(g) + Y2(g) X2Y(g) 2X2Y(g) 1 X2(g) + 2Y 2(g) The numerical value of Kc for reaction I is 2. Under the same conditions, what is the numerical value of Kc for reaction II? A 1 2 B 1 2 C 1 4 D –2 © UCLES 2007 9701/01/M/J/07 www.xtremepapers.net 5 10 The Boltzmann distribution shows the number of molecules having a particular kinetic energy at constant temperature. number of gas molecules having a given energy L M 0 N 0 kinetic energy Ea If the temperature is decreased by 10 °C, what happens to the size of the areas labelled L, M and N? L A B C D decreases decreases increases increases M decreases increases decreases decreases N decreases decreases decreases increases © UCLES 2007 9701/01/M/J/07 [Turn over www.xtremepapers.net 6 11 In the diagram, curve X was obtained by observing the decomposition of 100 cm3 of 1.0 mol dm–3 hydrogen peroxide, catalysed by manganese(IV) oxide. Y X volume of oxygen formed 0 0 time Which alteration to the original experimental conditions would produce curve Y? A B C D adding water adding some 0.1 mol dm–3 hydrogen peroxide using less manganese(IV) oxide lowering the temperature 12 Which chlorine compound has bonding that can be described as ionic with some covalent character? A NaCl B MgCl2 C AlCl3 D SiCl4 13 Al Cl3 reacts with LiAl H4 and (CH3)3N to give (CH3)3NAl H3. Which statement about (CH3)3NAl H3 is correct? A B C D It contains hydrogen bonding. It is dimeric. The Al atom has an incomplete octet of electrons. The bonds around the Al atom are tetrahedrally arranged. © UCLES 2007 9701/01/M/J/07 www.xtremepapers.net 7 14 Slaked lime, Ca(OH)2, may be made from limestone, CaCO3. On heating in a lime kiln at 1000 °C, limestone decomposes as follows. reaction 1 CaCO3(s) → CaO(s) + CO2(g) Water is then reacted with calcium oxide, CaO, as follows. reaction 2 CaO(s) + H2O(l) → Ca(OH)2(s) What are the enthalpy changes of these reactions? reaction 1 A B C D endothermic endothermic exothermic exothermic reaction 2 endothermic exothermic endothermic exothermic 15 In the treatment of domestic water supplies, chlorine is added to the water to form chloric(I) acid, HClO. Cl2(aq) + H2O(I) → H+(aq) + Cl –(aq) + HClO(aq) This reacts further to give the chlorate(I) ion. HClO(aq) + H2O(I) → H3O+(aq) + ClO–(aq) Both HClO and ClO– kill bacteria by oxidation. What is the change in oxidation number of chlorine in forming the chlorate(I) ion from the aqueous chlorine? A –1 B 0 C +1 D +2 16 The standard enthalpy changes of formation of HCl and HI are –92 kJ mol–1 and +26 kJ mol–1 respectively. Which statement is most important in explaining this difference? A B C D Chlorine is more electronegative than iodine. The activation energy for the H2 / Cl2 reaction is much less than that for the H2 / I2 reaction. The bond energy of HI is smaller than the bond energy of HCl. The bond energy of I2 is smaller than the bond energy of Cl2. © UCLES 2007 9701/01/M/J/07 [Turn over www.xtremepapers.net 8 17 Methyl mercaptan, CH3SH, is one of the substances responsible for bad breath and is often used to impart a smell to natural gas in a pipeline. What will be formed when CH3SH is burned in an excess of air? A B C D CO CO CO2 CO2 CO2 H2O H2O H2O H2S SO3 SO2 SO3 18 A solid nitrate fertiliser reacts with an alkali to produce a gas which turns damp pH paper blue. What is the empirical formula of this fertiliser? A NO3 B NHO3 C NH2O D N2H4O3 19 Glucose, C6H12O6, is a product of photosynthesis. It has the following structure. H H HO H H H C C C C C C H O OH H OH OH OH How many chiral centres does the molecule have? A 1 B 2 C 4 D 6 © UCLES 2007 9701/01/M/J/07 www.xtremepapers.net 9 20 Under the Montreal Protocol, the manufacture of chlorofluorocarbons has been phased out, and they are being replaced by fluorocarbons. One chlorofluorocarbon which was widely used as a solvent is CCl2FCCl F2. Large stocks of it remain. One process to use up these stocks is to convert it into the fluorocarbon CH2FCF3 by the following route. CCl2FCCl F2 step 1 CCl3CF3 step 2 CCl2FCF3 step 3 CH2FCF3 What type of reaction is step 2? A B C D electrophilic substitution free radical reduction isomerisation nucleophilic substitution 21 Which reagent could be used to convert CH3CO2CH3 into ClCH2CO2CH3? A B C D concentrated hydrochloric acid at 100 °C phosphorus pentachloride at room temperature sulphur dichloride oxide (thionyl chloride, SOCl2) at 50 °C chlorine in bright sunlight at 100 °C 22 In which reaction is a carbocation (carbonium ion) an intermediate? A B C D CH2=CH2 + Br2 CH3CH2Br + NaOH CH3CH3 + Cl2 CH3CHO + HCN CH2BrCH2Br CH3CH2OH + NaBr CH3CH2Cl + HCl CN– CH3CH(OH)CN 23 The compound 1,2-dichloroethene, C2H2Cl 2, has been used as an industrial solvent for a number of compounds including fats, camphor and caffeine. Which statement about this compound is incorrect? A B C D The compound can be catalytically hydrogenated. The compound is a planar molecule. The compound shows cis-trans isomerism. The compound shows optical isomerism. © UCLES 2007 9701/01/M/J/07 [Turn over www.xtremepapers.net 10 24 Which term describes the action of NaOH(aq) on a bromoalkane? A B C D acid-base reaction electrophilic substitution elimination of HBr nucleophilic substitution 25 X and Y are the reagents required to convert 1-bromopropane into butanoic acid. H H C H H C H H C H Br X H H C H H C H H C H CN Y H H C H H C H H C H C OH O What are the correct identities of X and Y? X A B C D NH3 KCN in C2H5OH KCN in C2H5OH HCN Y HCl(aq) NaOH(aq) HCl(aq) NaOH(aq) 26 An alcohol with molecular formula CnH2n+1OH has a chiral carbon atom but does not react with MnO − / H+. 4 What is the least number of carbon atoms such an alcohol could possess? A 5 B 6 C 7 D 8 27 Which reagent gives the same visible result with propanal and with propan-2-ol? A B C D 2,4-dinitrophenylhydrazine reagent acidified potassium dichromate(VI) sodium Tollens’ reagent © UCLES 2007 9701/01/M/J/07 www.xtremepapers.net 11 28 Compound X will decolourise a warm acidified solution of manganate(VII) ions and forms orange crystals on reaction with 2,4-dinitrophenylhydrazine. What is X? A B C D CH3CH=CHCH2OH CH3COCH2CH3 CH3CH2CH2CHO CH3CH(OH)CH2CO2H 29 Which compound would undergo nucleophilic addition? A B C D ethene, C2H4 bromoethane, C2H5Br ethanal, CH3CHO ethane, C2H6 30 Which formula represents the organic compound formed by the reaction of propanoic acid with methanol in the presence of concentrated sulphuric acid as a catalyst? A B C D CH3CH2COCH3 CH3CH2CO2CH3 CH3CO2CH2CH3 CH3CH2CH2CO2CH3 © UCLES 2007 9701/01/M/J/07 [Turn over www.xtremepapers.net 12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Use of the Data Booklet is relevant to this question. The technetium–99 isotope (99Tc) is radioactive and has been found in lobsters and seaweed adjacent to nuclear fuel reprocessing plants. Which statements are correct about an atom of 99Tc? 1 2 3 It has 13 more neutrons than protons. It has 43 protons. It has 99 nucleons. 32 Which of the following solids contain more than one type of chemical bond? 1 2 3 brass (an alloy of copper and zinc) graphite ice 33 Many crude oils contain sulphur as H2S. During refining, by the Claus process, the H2S is converted into solid sulphur, which is then removed. reaction I reaction II 2H2S(g) + 3O2(g) → 2H2O(l) + 2SO2(g) 2H2S(g) + SO2(g) → 2H2O(l) + 3S(s) Which statements about the Claus process are correct? 1 2 3 H2S is oxidised in reaction I. SO2 oxidises H2S in reaction II. SO2 behaves as a catalyst. © UCLES 2007 9701/01/M/J/07 www.xtremepapers.net 13 34 Two bulbs R and S, connected by a mercury manometer, are held in a thermostat, as shown. The volume of R is twice that of S. R contains gas, X, at the same pressure as the nitrogen in S. R S nitrogen thermostat manometer mercury X When the temperature is increased, which gases in bulb R would cause the mercury level in the right-hand limb of the manometer to rise? 1 2 3 an equilibrium mixture N2F4(g) an equilibrium mixture CH3NC(g) nitrogen 2NF2(g); ∆H positive CH3CN(g); ∆H negative 35 Which statements concerning the third period elements (sodium to argon) and their compounds are correct? 1 2 3 The elements become more electronegative from sodium to chlorine. Aluminium oxide is the only oxide which is insoluble in water. The maximum oxidation state is shown by silicon. 36 Use of the Data Booklet is relevant to this question. The element astatine lies below iodine in Group VII of the Periodic Table. What will be the properties of astatine? 1 2 3 It forms diatomic molecules which dissociate more readily than chlorine molecules. It reacts explosively with hydrogen. It is a good reducing agent. 37 Nitrogen and oxygen react in a hot car engine to form nitrogen monoxide which is a serious pollutant in our cities and in the countryside. However, nitrogen and oxygen do not react at room temperature. Which statements help to explain why nitrogen and oxygen do not react at room temperature? 1 2 3 The reaction is endothermic. A high activation energy is required. Nitrogen has a high bond energy. 9701/01/M/J/07 © UCLES 2007 [Turn over www.xtremepapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 38 What types of reaction are undergone by 2-bromopropane? 1 2 3 elimination free radical substitution nucleophilic substitution 39 Menthol, from oil of mint, is used in soaps and perfumes. CH3 CH CH2 CH2 CH CH CH3 CH3 menthol CH2 CH(OH) Which statements about menthol are correct? 1 2 3 There is a total of two chiral centres present in the menthol molecule. On reaction with concentrated sulphuric acid, menthol produces a mixture of two alkenes. A solution of acidified potassium dichromate(VI), on warming with menthol, changes colour from orange to green. 40 Fats and grease that build up on pans used in cooking are esters. Pans which are dirty from fats or grease may be cleaned by heating them with a reagent that will react with the ester group. What may be used to clean such pans by this reaction? 1 2 3 vinegar - aqueous ethanoic acid, CH3CO2H alcohol - ethanol, C2H5OH baking powder - sodium hydrogencarbonate, NaHCO3 © UCLES 2007 9701/01/M/J/07 www.xtremepapers.net 15 BLANK PAGE 9701/01/M/J/07 www.xtremepapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. 9701/01/M/J/07 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft Clean Eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 May/June 2008 1 hour *7255044678* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 16 printed pages. IB08 06_9701_01/2RP © UCLES 2008 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 In the Basic Oxygen steel-making process the P4O10 impurity is removed by reacting it with calcium oxide. The only product of this reaction is the salt calcium phosphate, Ca3(PO4)2. In this reaction, how many moles of calcium oxide react with one mole of P4O10? A 2 1 B 1.5 C 3 D 6 Use of the Data Booklet is relevant to this question. A typical solid fertiliser for use with household plants and shrubs contains the elements N, P, and K in the ratio of 15 g : 30 g :15 g per 100 g of fertiliser. The recommended usage of fertiliser is 14 g of fertiliser per 5 dm3 of water. What is the concentration of nitrogen atoms in this solution? A B C D 3 0.03 mol dm–3 0.05 mol dm–3 0.42 mol dm–3 0.75 mol dm–3 32 15 P Skin cancer can be treated using a radioactive isotope of phosphorus, containing the phosphide ion area. 32 15 3− . A compound P , wrapped in a plastic sheet, is strapped to the affected What is the composition of the phosphide ion, protons A B C D 15 15 17 32 neutrons 17 17 15 17 electrons 18 32 17 15 32 15 P3 − ? © UCLES 2008 9701/01/M/J/08 www.xtremepapers.net 3 4 When barium metal burns in oxygen, the ionic compound barium peroxide, BaO2, is formed. Which dot-and-cross diagram represents the electronic structure of the peroxide anion in BaO2? key A B C D electron from first oxygen atom electron from second oxygen atom electron from barium atom 5 In this question, the methyl group, CH3, is represented by Me. Trimethylamine, Me3N, reacts with boron trifluoride, BF3, to form a compound of formula Me3N.BF3. How may this reaction be written in terms of the shapes of the reactants and products? Me Me Me A Me N Me + F B F F F N B F Me Me Me B Me N Me + F B F F F N B F Me Me Me C Me N Me + F B F F F N B F Me Me Me D Me N Me + F B F F B F F F N Me F Me Me F Me F © UCLES 2008 9701/01/M/J/08 [Turn over www.xtremepapers.net 4 6 The density of ice is 1.00 g cm–3. What is the volume of steam produced when 1.00 cm3 of ice is heated to 323 °C (596 K) at a pressure of one atmosphere (101 kPa)? [1 mol of a gas occupies 24.0 dm3 at 25 °C (298 K) and one atmosphere.] A 7 0.267 dm3 B 1.33 dm3 C 2.67 dm3 D 48.0 dm3 Which pair of elements have bonds of the same type between their atoms in the solid state? A B C D aluminium and phosphorus chlorine and argon magnesium and silicon sulphur and chlorine 8 Which diagram correctly describes the behaviour of a fixed mass of an ideal gas? (T is measured in K.) A constant T p pV B constant T pV C constant T V D constant p 0 0 V 0 0 p 0 0 V 0 0 T 9 For which equation does the enthalpy change correspond to the enthalpy change of atomisation of iodine? A B C D ½ I2(s) → I(s) ½ I2(s) → I(g) I2(g) → 2I(g) I2(s) → 2I(g) © UCLES 2008 9701/01/M/J/08 www.xtremepapers.net 5 10 Titanium occurs naturally as the mineral rutile, TiO2. One possible method of extraction of titanium is to reduce the rutile by heating with carbon. TiO2(s) + 2C(s) → Ti(s) + 2CO(g) The standard enthalpy changes of formation of TiO2(s) and CO(g) are –940 kJ mol–1 and –110 kJ mol–1 respectively. What is the standard enthalpy change of this reaction? A B C D –830 kJ mol–1 –720 kJ mol–1 +720 kJ mol–1 +830 kJ mol–1 11 For the reaction W(aq) + 2X(aq) 2Y(aq) + 3Z(aq) what are the correct units for the equilibrium constant Kc? A mol dm–3 B mol2 dm–6 C mol–1 dm3 D mol–2 dm6 © UCLES 2008 9701/01/M/J/08 [Turn over www.xtremepapers.net 6 12 The molecular energy distribution curve represents the variation in energy of the molecules of a gas at room temperature. proportion of molecules 0 0 energy Which curve applies for the same gas at a lower temperature? A B proportion of molecules proportion of molecules 0 0 energy C 0 0 energy D proportion of molecules proportion of molecules 0 0 energy 0 0 energy 13 In an experiment, 0.1 g samples of Na2O, MgO, P4O10 and SO2 are added to separate 100 cm3 volumes of water. For which oxide is the resulting mixture most alkaline? A Na2O B MgO C P4O10 D SO2 © UCLES 2008 9701/01/M/J/08 www.xtremepapers.net 7 14 Which element is expected to show the greatest tendency to form some covalent compounds? A B C D aluminium calcium magnesium sodium 15 Use of the Data Booklet is relevant to this question. The combustion of fossil fuels is a major source of increasing atmospheric carbon dioxide, with a consequential rise in global warming. Another significant contribution to carbon dioxide levels comes from the thermal decomposition of limestone, in the manufacture of cement and of lime for agricultural purposes. Cement works roast 1000 million tonnes of limestone per year and a further 200 million tonnes is roasted in kilns to make lime. What is the total annual mass output of carbon dioxide (in million tonnes) from these two processes? A 440 B 527 C 660 D 880 16 Properties of chlorine, iodine and their compounds are compared. Property Q for chlorine is smaller than for iodine. What is property Q? A B C D oxidising ability of the element solubility of the silver halide in NH3(aq) strength of van der Waals’ forces between the molecules of the element thermal stability of the hydrogen halide 17 Which reagent, when mixed and heated with ammonium sulphate, liberates ammonia? A B C D aqueous bromine dilute hydrochloric acid limewater acidified potassium dichromate(VI) © UCLES 2008 9701/01/M/J/08 [Turn over www.xtremepapers.net 8 18 The diagram represents the Haber process for the manufacture of ammonia from nitrogen and hydrogen. heat exchanger N2 + H2 catalytic converter condenser NH3 What is the purpose of the heat exchanger? A B C D to cool the incoming gas mixture to avoid overheating the catalyst to cool the reaction products and separate the NH3 from unused N2 and H2 to warm the incoming gas mixture and shift the equilibrium to give more NH3 to warm the incoming gas mixture and speed up the reaction 19 Total elimination of the pollutant sulphur dioxide, SO2, is difficult, both for economic and technical reasons. Its emission can be reduced in furnace chimneys using desulphurisation plants, where the gases are scrubbed (washed) with calcium hydroxide to remove the SO2. What is the main product formed initially? A CaO B Ca(OH)2 C CaSO3 D CaSO4 20 Which pair of reaction types is illustrated by the reaction sequence below? CH3CH=CHCH3 HI in CH3CO2H CH3CH2CHICH3 NaOH(aq) CH3CH2CH(OH)CH3 A B C D electrophilic addition and electrophilic substitution electrophilic addition and nucleophilic substitution nucleophilic addition and electrophilic substitution nucleophilic addition and nucleophilic substitution © UCLES 2008 9701/01/M/J/08 www.xtremepapers.net 9 21 Trichloroethene is widely used as a dry-cleaning agent. H C Cl C Cl Cl With which of the following does trichloroethene react to give a chiral product? A Br2 B HCl C NaCN(aq) D NaOH(aq) 22 Chloroethene, CH2=CHCl, is the monomer of PVC. What are the C−C−C bond angles along the polymeric chain in PVC? A B C D They are all 109.5°. Half are 109.5° and half are 120°. They are all 120°. They are all 180°. 23 Which hydrocarbon would not be collected in the inverted tube by heating pentane, CH3(CH2)3CH3, in the apparatus shown? pentane on mineral fibre aluminium oxide hydrocarbons very strong heat water A B C D CH4 CH3CH3 CH3CH2CH=CH2 CH3(CH2)8CH3 © UCLES 2008 9701/01/M/J/08 [Turn over www.xtremepapers.net 10 24 Mevalonic acid, 3,5-dihydroxy-3-methylpentanoic acid, is involved in cholesterol formation in the body. It is an oil that occurs as a mixture of the two interchanging molecules shown in the diagram. HO C CH2 CH2 CH2OH CO2H CH3 I II HO C CH2 CH2 O CH3 CH2 C O What names are used to describe the pair of interchanging reactions I and II? A B C D condensation and addition dehydrogenation and hydrogenation esterification and hydrolysis neutralisation and acidification 25 Halogenoalkanes are important molecules in organic synthetic reactions. In particular they undergo a range of nucleophilic reactions. Which reaction proceeds only by an SN1 mechanism? A B C D CH3CH2Br + NH3 CH3CH2CH2I + OH– CH3CHBrCH3 + NH3 (CH3)3CI + OH– 26 An alcohol of molecular formula C4H10O2 contains two OH groups and has an unbranched carbon atom chain. On reaction with an excess of hot MnO− / H+ this alcohol is converted into a compound of 4 molecular formula C4H6O4. To which two carbon atoms in the chain of the alcohol are the two OH groups attached? A B C D 1st and 2nd 1st and 3rd 1st and 4th 2nd and 3rd © UCLES 2008 9701/01/M/J/08 www.xtremepapers.net 11 27 Compound X • • has the molecular formula C10H14O; is unreactive towards mild oxidising agents. What is the structure of the compound formed by dehydration of X? A CH2 CH2 CH CH2 CH2 B CH CH CH3 C CH3 CH CH CH2 D CH3 C CH CH3 28 Ethanal, CH3CHO, can be reduced using an aqueous methanolic solution of NaBH4 as the reducing agent. This is a nucleophilic addition reaction. What could be the first step of this mechanism? A B C D attack of an H+ ion at the carbon atom of the carbonyl group attack of an H+ ion at the oxygen atom of the carbonyl group attack of an H– ion at the carbon atom of the carbonyl group attack of an H– ion at the oxygen atom of the carbonyl group 29 Which compound is both chiral and acidic? A H C C H CO2H CO2H B CH3 OH C CH2Br HCO2CH CH3 D CH(OH)CO2H CH2CO2H © UCLES 2008 9701/01/M/J/08 [Turn over www.xtremepapers.net 12 30 Compound X, C6H12O, is oxidised by acidified sodium dichromate(VI) to compound Y. Compound Y reacts with ethanol in the presence of a little concentrated sulphuric acid to give liquid Z. What is the formula of Z? A B C D CH3(CH2)2CH=CHCO2H CH3(CH2)4CH2COCH2CH3 CH3(CH2)4CO2CH2CH3 CH3CH2CO2(CH2)4CH3 © UCLES 2008 9701/01/M/J/08 www.xtremepapers.net 13 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 For complete combustion, 1 mol of an organic compound X was found to require 2.5 mol of molecular oxygen. Which compounds could be X? 1 2 3 C2H5OH C2H2 CH3CHO 32 Catalysts are used in many reversible reactions in the chemical industry. Vanadium(V) oxide is used in this way in the Contact process for the formation of SO3. 2SO2(g) + O2(g) 2SO3(g) What effect does vanadium(V) oxide have on this equilibrium? 1 2 3 It speeds up the forward reaction. It increases the value of Kp. It increases the value of Ea for the reverse reaction. 33 Which statements about the properties of a catalyst are correct? 1 2 3 A catalyst increases the average kinetic energy of the reacting particles. A catalyst increases the rate of the reverse reaction. A catalyst has no effect on the enthalpy change of the reaction. © UCLES 2008 9701/01/M/J/08 [Turn over www.xtremepapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 34 Water is added to anhydrous aluminium chloride to make a 0.1 mol dm-3 solution. Which observations are correct? 1 2 3 The reaction is endothermic. The solution is acidic. The solution contains the ion [Al(H2O)6]3+. 35 The electronic structure of the outer shell of the element radium is 7s2. Which statements will be correct for radium within its group? 1 2 3 The element will decompose water, liberating hydrogen. The element will show an oxidation number of +2 in all its compounds. Radium has the highest first ionisation energy. 36 When the yellow liquid NCl3 is stirred into aqueous sodium hydroxide, the reaction that occurs can be represented by the following equation. 2NCl3(l) + 6NaOH(aq) → N2(g) + 3NaCl (aq) + 3NaOCl (aq) + 3H2O(l) What will be the result of this reaction? 1 2 3 The nitrogen is oxidised. A bleaching solution remains after the reaction. The final solution gives a precipitate with acidified silver nitrate. © UCLES 2008 9701/01/M/J/08 www.xtremepapers.net 15 37 Aspirin is a widely-available pain-killer, whose properties have been known for centuries. The structure of aspirin is shown. OH C O O C CH3 O Which functional groups are present in aspirin? 1 2 3 alcohol carboxylic acid ester 38 The structure of monosodium glutamate, a flavour enhancer, is shown. Na+ O– C O CH2 CH2 CH NH2 CO2H It may be prepared starting from the following compound. Cl CH2 CH2 CH NH2 CO2H Which set of reagents and reaction conditions could be used to prepare monosodium glutamate? 1 2 3 Heat under reflux with ethanolic KCN followed by hydrolysis with NaOH(aq). − Heat with sodium methanoate, HCO2 Na+ . Heat under reflux with NaOH(aq). © UCLES 2008 9701/01/M/J/08 [Turn over www.xtremepapers.net 16 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 39 The compound cholesterol has the following structure. CH3 CH CH2 CH2 CH HO CH2 CH3 CH C C CH CH3 CH C CH CH2 CH2 CH2 CH2 CH2 CH CH3 CH3 Which statements are correct? 1 2 3 Cholesterol reacts with a mixture of ethanoic acid and concentrated sulphuric acid. Cholesterol reacts with bromine to form a compound which has two new chiral centres. Cholesterol is oxidised by acidified sodium dichromate(VI) to form an aldehyde. 40 Ferulic acid is an antioxidant that occurs widely in plants. HO CH3O ferulic acid CH=CHCO2H Which reagents can react with the –CH=CHCO2H part of the molecule? 1 2 3 NaOH(aq) acidified KMnO4 HBr Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2008 9701/01/M/J/08 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice 9701/01 May/June 2009 1 hour Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet Additional Materials: *5448023915* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 15 printed pages and 1 blank page. IB09 06_9701_01/5RP © UCLES 2009 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Use of the Data Booklet is relevant to this question. In leaded petrol there is an additive composed of lead, carbon and hydrogen only. This compound contains 29.7 % carbon and 6.19 % hydrogen by mass. What is the value of x in the empirical formula PbC8HX? A 5 B 6 C 16 D 20 2 A household bleach contains sodium chlorate(I), NaClO, as its active ingredient. The concentration of NaClO in the bleach can be determined by reacting a known amount with aqueous hydrogen peroxide, H2O2. NaClO(aq) + H2O2(aq) → NaCl(aq) + O2(g) + H2O(l) When 25.0 cm3 of bleach is treated with an excess of aqueous H2O2, 0.0350 mol of oxygen gas is given off. What is the concentration of NaClO in the bleach? A B C D 8.75 × 10–4 mol dm–3 0.700 mol dm–3 0.875 mol dm–3 1.40 mol dm–3 3 The first seven ionisation energies of an element between lithium and neon in the Periodic Table are as follows. 1310 3390 5320 7450 11 000 13 300 71 000 kJ mol–1 What is the outer electronic configuration of the element? A 2s2 B 2s22p1 C 2s22p4 D 2s22p6 © UCLES 2009 9701/01/M/J/09 www.xtremepapers.net 3 4 Use of the Data Booklet is relevant to this question. Which graph represents the number of unpaired p orbital electrons for atoms with proton numbers 13 to 18? A B number of unpaired electrons number of unpaired electrons 0 13 14 15 16 17 proton number 18 0 13 14 15 16 17 proton number 18 C D number of unpaired electrons number of unpaired electrons 0 13 14 15 16 17 proton number 18 0 13 14 15 16 17 proton number 18 5 Which statement explains why the boiling point of methane is higher than that of neon? [Ar: H, 1; C, 12; Ne, 20] A B C D A molecule of methane has a greater mass than a molecule of neon. Molecules of methane form hydrogen bonds, but those of neon do not. Molecules of methane have stronger intermolecular forces than those of neon. The molecule of methane is polar, but that of neon is not. © UCLES 2009 9701/01/M/J/09 [Turn over www.xtremepapers.net 4 6 In which reaction does the carbon-containing product have a smaller bond angle than the organic reactant? A B C D 7 bromoethane refluxed with ethanolic sodium hydroxide complete combustion of methane in air methane and an excess of chlorine under ultraviolet light polymerisation of ethene A crystal of iodine produces a purple vapour when gently heated. Which pair of statements correctly describes this process? type of bond broken A B C D covalent covalent induced dipole-dipole permanent dipole-dipole formula of purple species I I2 I2 I2 8 Hydrogen peroxide slowly decomposes into water and oxygen. The enthalpy change of reaction can be calculated using standard enthalpies of formation. (hydrogen peroxide(l)) = –187.8 kJ mol–1 (water(l)) = –285.8 kJ mol–1 Using a Hess cycle, what is the enthalpy change of reaction for this decomposition? 2H2O2(l) → 2H2O(l) + O2(g) A B C D +98 kJ mol–1 −98 kJ mol–1 −196 kJ mol–1 −947.2 kJ mol–1 © UCLES 2009 9701/01/M/J/09 www.xtremepapers.net 5 9 When copper is extracted from its ores, the metal is not pure enough for electrical uses. The impure copper, which contains small amounts of silver and gold, is purified by electrolysis. During this process a ‘sludge’ forms beneath the anode which is found to contain silver and traces of gold. Why is silver found in this sludge? A B C D Silver is less electropositive than copper. Silver is more dense than copper and falls off the cathode. Silver reacts with the electrolyte to form an insoluble chloride salt. Silver reacts with the electrolyte to form an insoluble sulfate salt. 10 The diagram shows the Maxwell-Boltzmann energy distribution curve for molecules of a mixture of two gases at a given temperature. For a reaction to occur the molecules must collide together with sufficient energy. number of molecules 0 0 energy Ea2 Ea1 Ea is the activation energy for the reaction between the gases. Of the two values shown, one is for a catalysed reaction, the other for an uncatalysed one. Which pair of statements is correct when a catalyst is used? A B C D Ea1 Ea1 Ea1 Ea1 catalysed reaction fewer effective collisions uncatalysed reaction fewer effective collisions catalysed reaction more effective collisions uncatalysed reaction more effective collisions Ea2 Ea2 Ea2 Ea2 uncatalysed reaction more effective collisions catalysed reaction more effective collisions uncatalysed reaction fewer effective collisions catalysed reaction fewer effective collisions © UCLES 2009 9701/01/M/J/09 [Turn over www.xtremepapers.net 6 11 In some fireworks there is a reaction between powdered aluminium and powdered barium nitrate in which heat is evolved and an unreactive gas is produced. What is the equation for this reaction? A B C D 2Al + Ba(NO3)2 → Al2O3 + BaO + 2NO 4Al + 4Ba(NO3)2 → 2Al2O3 + 4Ba(NO2)2 + O2 10Al + 3Ba(NO3)2 → 5Al2O3 + 3BaO + 3N2 10Al + 18Ba(NO3)2 → 10Al(NO3)3 + 18BaO + 3N2 12 Which group of particles is in order of increasing size? A B C D N N3– Na+ Na+ O O2– Mg2+ Ne F F– Al 3+ F– 2 − − 13 River water in a chalky agricultural area may contain Ca2+, Mg2+, CO 3 − , HCO 3 , Cl − and NO 3 ions. In a waterworks, such water is treated by adding a calculated quantity of calcium hydroxide. What will be precipitated following the addition of calcium hydroxide? A B C D CaCl2 CaCO3 Ca(NO3) 2 Mg(NO3)2 14 Over half a million tonnes of bromine are manufactured annually and are mainly used for making other compounds. One important use is for agricultural chemicals. What is another important use for bromine? A B C D antiseptic agents bleaches for textiles and the paper industry flame-retardants and fire extinguishers water purification © UCLES 2009 9701/01/M/J/09 www.xtremepapers.net 7 15 In black and white photographic film, light converts silver chloride into metallic silver. After the film has been developed, the unreacted silver chloride is removed by reaction with sodium thiosulfate to produce a ‘fixed’ negative. AgCl + 2Na2S2O3 → 4Na+ + Cl – + [Ag(S2O3)2]3– What is the function of the thiosulfate ion? A B C D to make the silver ions soluble to oxidise the silver ions to oxidise the silver metal to reduce the silver ions 16 Which statement is most likely to be true for astatine, which is below iodine in Group VII of the Periodic Table? A B C D Astatine and aqueous potassium chloride react to form aqueous potassium astatide and chlorine. Potassium astatide and hot dilute sulfuric acid react to form white fumes of only hydrogen astatide. Silver astatide reacts with dilute aqueous ammonia in excess to form a solution of a soluble complex. Sodium astatide and hot concentrated sulfuric acid react to form astatine. 17 Deposits of ammonium compounds have been discovered in areas of high atmospheric pollution. They are believed to arise from the following reaction. SO3 + H2O + 2NH3 → (NH4)2SO4 What does not occur in this reaction? A B C D acid / base neutralisation dative bond formation ionic bond formation oxidation / reduction © UCLES 2009 9701/01/M/J/09 [Turn over www.xtremepapers.net 8 18 Mohr’s salt is a pale green crystalline solid which is soluble in water. It is a ‘double sulfate’ which contains two cations, one of which is Fe2+. The identity of the second cation was determined by heating solid Mohr’s salt with solid sodium hydroxide and a colourless gas was evolved. The gas readily dissolved in water giving an alkaline solution. A grey-green solid residue was also formed which was insoluble in water. What are the identities of the gas and the solid residue? gas A B C D H2 NH3 NH3 SO2 residue FeSO4 Na2SO4 Fe(OH)2 Fe(OH)2 19 In recent years a number of athletes have been banned from sports because of their illegal use of synthetic testosterone, a naturally occurring hormone in the body. CH3 CH3 OH O testosterone How many chiral centres are present in a testosterone molecule? A 1 B 2 C 3 D 6 20 The compound known as ‘gamma-linolenic acid’ is found in significant amounts in the seeds of the Evening Primrose plant. There is evidence that the compound may help patients with diabetes. CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4CO2H gamma-linolenic acid How many cis-trans isomers does gamma-linolenic acid have? A 3 B 6 C 8 D 12 © UCLES 2009 9701/01/M/J/09 www.xtremepapers.net 9 21 What always applies to a nucleophile? A B C D It attacks a double bond. It has a lone pair of electrons. It is a single atom. It is negatively charged. 22 Trichloroethanoic acid, CCl3CO2H, is used in cosmetic surgery to perform a ‘chemical peel’ to remove dead skin. Trichloroethanoic acid can be made by reacting chlorine with ethanoic acid. What is the mechanism of this reaction? A B C D electrophilic addition electrophilic substitution free radical addition free radical substitution 23 Polymerisation of chloroethene gives PVC. How does the carbon-carbon bond in PVC compare with that in chloroethene? A B C D longer and stronger longer and weaker shorter and stronger shorter and weaker 24 In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group? attacking group A B C D electrophile electrophile nucleophile nucleophile leaving group electrophile nucleophile electrophile nucleophile © UCLES 2009 9701/01/M/J/09 [Turn over www.xtremepapers.net 10 25 Which reaction would not give propene as one product? A B C D adding an excess of concentrated sulfuric acid to propan-1-ol adding warm aqueous sodium hydroxide to 2-bromopropane adding warm ethanolic sodium hydroxide to 1-bromopropane passing propan-2-ol vapour over heated aluminium oxide 26 Glycol, used in anti-freeze, has the formula HOCH2CH2OH. It can be oxidised to give a number of products. What is the molecular formula of an oxidation product of glycol that will not react with sodium? A C2H2O2 B C2H2O3 C C2H2O4 D C2H4O2 27 Which ester is formed when the alcohol CH3CH2OH is reacted with CH3CH2CH2CO2H? A B C D ethyl propanoate ethyl butanoate propyl ethanoate butyl ethanoate 28 Carvone gives the characteristic flavour to caraway and spearmint. O CH3 H3C C CH2 carvone Prolonged heating of carvone with hot concentrated acidified potassium manganate(VII) produces carbon dioxide and a compound X. X contains nine carbon atoms and reacts with 2,4-dinitrophenylhydrazine reagent. What is the maximum number of molecules of 2,4-dinitrophenylhydrazine that will react with one molecule of X? A 1 B 2 C 3 D 4 © UCLES 2009 9701/01/M/J/09 www.xtremepapers.net 11 29 2-Methylbuta-1,3-diene, CH2=C(CH3)–CH=CH2, is used as a monomer in the manufacture of synthetic rubbers. Which compound would not produce this monomer on treatment with concentrated sulfuric acid at 170 °C? A B C D (CH3)2C(OH)CH(OH)CH3 HOCH2CH(CH3)CH2CH2OH HOCH2CH(CH3)CH(OH)CH3 HOCH2C(CH3)(OH)CH2CH3 30 A compound Y has the following properties. • It is a liquid at room temperature and atmospheric pressure. • It does not mix completely with water. • It does not decolourise acidified potassium manganate(VII). What could Y be? A B C D ethane ethanoic acid ethanol ethyl ethanoate © UCLES 2009 9701/01/M/J/09 [Turn over www.xtremepapers.net 12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 12 31 On a scale in which the mass of a sample of chlorine is 72. C atom is 12 the relative molecular mass of a particular Which properties of the atoms in this sample are always the same? 1 2 3 radius nucleon number isotopic mass 32 An ideal gas obeys the gas laws under all conditions of temperature and pressure. Which of the following are true for an ideal gas? 1 2 3 The molecules have negligible volume. There are no forces of attraction between molecules. The molecules have an average kinetic energy which is proportional to its absolute temperature. 33 For which reactions does the value of ∆Ho represent both a standard enthalpy change of combustion and a standard enthalpy change of formation? 1 2 3 C(s) + O2(g) → CO2(g) 2C(s) + O2(g) → 2CO(g) CO(g) + 1 2 O2(g) → CO2(g) © UCLES 2009 9701/01/M/J/09 www.xtremepapers.net 13 34 The following reaction takes place using liquid ammonia as a solvent. − Na+ NH2 + NH+ Cl − → Na+ Cl − + 2NH3 4 Which statements best explain why this reaction should be classified as a Brønsted-Lowry acidbase reaction? 1 2 3 The ammonium ion acts as a proton donor. Na+ Cl − is a salt. Ammonia is always basic. 35 The rock dolomite is a double carbonate of magnesium and calcium, CaCO3.MgCO3. When heated strongly, a product called calcined dolomite is formed which is used to line some furnaces for the production of metals. Why is calcined dolomite used for this purpose? 1 2 3 It is a refractory material. It will absorb acidic impurities in metallurgical processes. It will reduce metallic oxides to metals. 36 Which properties in the sequence hydrogen chloride, hydrogen bromide and hydrogen iodide steadily increase? 1 2 3 thermal stability bond length ease of oxidation © UCLES 2009 9701/01/M/J/09 [Turn over www.xtremepapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 37 A fraction of distilled crude oil contains molecules with between 15 and 19 carbon atoms. This fraction is cracked by strong heating. Why is this done? 1 2 3 To produce alkenes. To produce smaller molecules which are in higher demand. To insert oxygen atoms into the hydrocarbons. 38 Geraniol is one of several compounds produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the entrances to their hives. OH geraniol Which reactions will geraniol undergo? 1 2 3 reaction with hot concentrated acidic KMnO4 to give propanone addition of halogens reaction with aqueous NaHCO3 to give CO2 39 How can the rate of reaction between ethanal and aqueous hydrogen cyanide be increased? 1 2 3 by irradiation with ultraviolet light by a rise in temperature by the addition of a small quantity of aqueous sodium cyanide © UCLES 2009 9701/01/M/J/09 www.xtremepapers.net 15 40 A sun protection cream contains the following ester as its active ingredient. CH2CH3 CH3O CH CHCO2CH2CH CH2CH2CH2CH3 What are the products of its partial or total hydrolysis by aqueous sodium hydroxide? 1 CH3CH2CH2CH2CH(CH2CH3)CH2OH CH3O CH3O CH CHCO– Na+ 2 2 3 – CO2 Na+ © UCLES 2009 9701/01/M/J/09 www.xtremepapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. 9701/01/M/J/09 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/11 May/June 2010 1 hour *9264472640* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 14 printed pages and 2 blank pages. IB10 06_9701_11/4RP © UCLES 2010 [Turn over www.XtremePapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Use of the Data Booklet is relevant to this question. What could be the proton number of an element that has three unpaired electrons in each of its atoms? A 2 5 B 13 C 15 D 21 Use of the Data Booklet is relevant to this question. The elements radon (Rn), francium (Fr) and radium (Ra) have consecutive proton numbers in the Periodic Table. What is the order of their first ionisation energies? least endothermic A B C D Fr Fr Ra Rn Ra Rn Fr Ra most endothermic Rn Ra Rn Fr 3 Which gas closely approaches ideal behaviour at room temperature and pressure? A B C D ammonia carbon dioxide helium oxygen © UCLES 2010 9701/11/M/J/10 www.XtremePapers.net 3 4 Some bond energy values are listed below. bond C–H C–Cl Cl–Cl Br–Br bond energy / kJ mol–1 410 340 244 193 These bond energy values relate to the following four reactions. P Q R S Br2 → 2Br 2Cl → Cl2 CH3 + Cl → CH3Cl CH4 → CH3 + H What is the order of enthalpy changes of these reactions from most negative to most positive? A B C D 5 P→Q→R→S Q→R→S→P R→Q→P→S S→P→Q→R Given the following enthalpy changes, I2(g) + 3Cl2(g) → 2ICl3(s) I2(s) → I2(g) ∆Ho = –214 kJ mol–1 ∆Ho = +38 kJ mol–1 What is the standard enthalpy change of formation of iodine trichloride, ICl3(s)? A B C D 6 +176 kJ mol–1 –88 kJ mol–1 –176 kJ mol–1 –214 kJ mol–1 Ammonium nitrate, NH4NO3, can decompose explosively when heated. NH4NO3 → N2O + 2H2O What are the changes in the oxidation numbers of the two nitrogen atoms in NH4NO3 when this reaction proceeds? A –2, –4 B +2, +6 C +4, –6 D +4, –4 © UCLES 2010 9701/11/M/J/10 [Turn over www.XtremePapers.net 4 7 The Haber process for the manufacture of ammonia is represented by the following equation. N2(g) + 3H2(g) 2NH3(g) ∆H = –92 kJ mol–1 Which statement is correct about this reaction when the temperature is increased? A B C D 8 Both forward and backward rates increase. The backward rate only increases. The forward rate only increases. There is no effect on the backward or forward rate. Use of the Data Booklet is relevant to this question. 2.920 g of a Group II metal, X, reacts with an excess of chlorine to form 5.287 g of a compound with formula XCl2. What is metal X? A B C D barium calcium magnesium strontium 9 Which mass of gas would occupy a volume of 3 dm3 at 25 °C and 1 atmosphere pressure? [1 mol of gas occupies 24 dm3 at 25 °C and 1 atmosphere pressure.] A B C D 3.2 g O2 gas 5.6 g N2 gas 8.0 g SO2 gas 11.0 g CO2 gas © UCLES 2010 9701/11/M/J/10 www.XtremePapers.net 5 10 The table gives the concentrations and pH values of the aqueous solutions of two compounds, X and Y. Either compound could be an acid or a base. X concentration pH Student P concluded that X is a strong acid. Student Q concluded that the extent of dissociation is lower in X(aq) than in Y(aq). Which of the students are correct? A B C D both P and Q neither P nor Q P only Q only 2 mol dm–3 6 Y 2 mol dm–3 9 11 Swimming pool water can be kept free of harmful bacteria by adding aqueous sodium chlorate(I), NaOCl. This reacts with water to produce HOCl molecules which kill bacteria. OCl –(aq) + H2O OH–(aq) + HOCl (aq) In bright sunshine, the OCl – ion is broken down by ultra-violet light. OCl –(aq) + uv light → Cl –(aq) + ½O2(g) Which method would maintain the highest concentration of HOCl (aq)? A B C D acidify the pool water add a solution of chloride ions add a solution of hydroxide ions bubble air through the water © UCLES 2010 9701/11/M/J/10 [Turn over www.XtremePapers.net 6 12 Na2S2O3 reacts with dilute HCl to give a pale yellow precipitate. If 1 cm3 of 0.1 mol dm–3 HCl is added to 10 cm3 of 0.02 mol dm–3 Na2S2O3 the precipitate forms slowly. If the experiment is repeated with 1 cm3 of 0.1 mol dm–3 HCl and 10 cm3 of 0.05 mol dm–3 Na2S2O3 the precipitate forms more quickly. Why is this? A B C D The activation energy of the reaction is lower when 0.05 mol dm–3 Na2S2O3 is used. The reaction proceeds by a different pathway when 0.05 mol dm–3 Na2S2O3 is used. The collisions between reactant particles are more violent when 0.05 mol dm–3 Na2S2O3 is used. The reactant particles collide more frequently when 0.05 mol dm–3 Na2S2O3 is used. 13 How does concentrated sulfuric acid behave when it reacts with sodium chloride? A B C D as an acid only as an acid and oxidising agent as an oxidising agent only as a reducing agent only 14 X is a salt of one of the halogens chlorine, bromine, iodine, or astatine (proton number 85). The reaction scheme shows a series of reactions using a solution of X as the starting reagent. X HNO3(aq) AgNO3(aq) a precipitate an excess of dilute NH3(aq) a colourless solution an excess of HNO3(aq) a precipitate What could X be? A B C D sodium chloride sodium bromide potassium iodide potassium astatide © UCLES 2010 9701/11/M/J/10 www.XtremePapers.net 7 15 The percentage of ammonia obtainable, if equilibrium were established during the Haber process, is plotted against the operating pressure for two temperatures, 400 °C and 500 °C. Which diagram correctly represents the two graphs? A 40 % NH3 at 20 equilibrium 400 °C 500 °C 40 % NH3 at 20 equilibrium B 500 °C 400 °C 0 0 10 20 pressure / 103 kPa 0 0 10 20 pressure / 103 kPa C 40 % NH3 at 20 equilibrium 500 °C 0 0 10 20 pressure / 103 kPa 400 °C 40 % NH3 at 20 equilibrium D 500 °C 400 °C 0 0 10 20 pressure / 103 kPa 16 Consecutive elements X, Y, Z are in the third period of the Periodic Table. Element Y has the highest first ionisation energy and the lowest melting point. What could be the identities of X, Y and Z? A B C D aluminium, silicon, phosphorus magnesium, aluminium, silicon silicon, phosphorus, sulfur sodium, magnesium, aluminium 17 Which property of Group II elements (beryllium to barium) decreases with increasing atomic number? A B C D reactivity with water second ionisation energy solubility of hydroxides stability of the carbonates © UCLES 2010 9701/11/M/J/10 [Turn over www.XtremePapers.net 8 18 Which element of the third period requires the least number of moles of oxygen for the complete combustion of 1 mol of the element? A B C D aluminium magnesium phosphorus sodium 19 Two properties of non-metallic elements and their atoms are as follows. property 1 property 2 has an oxide that can form a strong acid in water has no paired 3p electrons Which properties do phosphorus and sulfur have? phosphorus A B C D 1 and 2 1 only 1 and 2 2 only sulfur 1 only 1 and 2 1 and 2 1 only 20 When gaseous chemicals are transported by road or by rail they are classified as follows. flammable non-flammable poisonous Which commonly transported gas is non-flammable? A B C D butane hydrogen oxygen propene © UCLES 2010 9701/11/M/J/10 www.XtremePapers.net 9 21 When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical substitution. In a propagation step the free radical X• is formed. CH3 CH3CH2 C CH3 CH3 + Cl ● → X● + HCl How many different forms of X• are possible? A 1 B 2 with C the 3 two D isomeric 4 alcohols, (CH3)3CCH2OH and 22 What will react differently (CH3)2CHCH2CH2OH? A B C D acidified aqueous potassium manganate(VII) concentrated sulfuric acid phosphorus pentachloride sodium 23 Which reagent will give similar results with both butanone and butanal? A B C D acidified aqueous potassium dichromate(VI) an alkaline solution containing complexed Cu2+ ions (Fehling’s solution) an aqueous solution containing [Ag(NH3)2]+ (Tollens’ reagent) 2,4-dinitrophenylhydrazine reagent 24 What is formed when propanone is refluxed with a solution of NaBH4? A B C D propanal propan-1-ol propan-2-ol propane 25 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D − C3H7CO 2 Na + © UCLES 2010 9701/11/M/J/10 [Turn over www.XtremePapers.net 10 26 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated? A B C D It destroys the ozone layer. It does not burn easily. It is easily biodegradable. Its combustion products are harmful. 27 Polymerisation of 1,1-dichloroethene produces a dense, high melting point substance that does not allow gases to pass through. It is used as cling wrapping. Which sequence appears in a short length of the polymer chain? A B C D [ CH2CCl2CH2CCl2CH2CCl2 ] [ CHClCHClCHClCHClCHClCHCl ] [ CCl2CCl2CCl2CCl2CCl2CCl2 ] [ CH2CCl2CHClCHClCH2CCl2 ] 28 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration of OH– ions present. Which is the most likely molecular structure of Y? A B C D CH3CH2CH2CH2Br CH3CH2CHBrCH3 (CH3)2CHCH2Br (CH3)3CBr 29 Which isomer of C4H10O forms three alkenes on dehydration? A B C D butan-1-ol butan-2-ol 2-methylpropan-1-ol 2-methylpropan-2-ol © UCLES 2010 9701/11/M/J/10 www.XtremePapers.net 11 30 Which compound exhibits both cis-trans and optical isomerism? A B C D CH3CH=CHCH2CH3 CH3CHBrCH=CH2 CH3CBr=CBrCH3 CH3CH2CHBrCH=CHBr © UCLES 2010 9701/11/M/J/10 [Turn over www.XtremePapers.net 12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Which diagrams represent part of a giant molecular structure? 1 =C 2 =C 3 = Na = Cl 32 Which reactions are redox reactions? 1 2 3 CaBr2 + 2H2SO4 → CaSO4 + Br2 + SO2 + 2H2O CaBr2 + 2H3PO4 → Ca(H2PO4)2 + 2HBr CaBr2 + 2AgNO3 → Ca(NO3)2 + 2AgBr 33 Sodium hydrogensulfide, NaSH, is used to remove hair from animal hides. Which statements about the SH– ion are correct? 1 2 3 It contains 18 electrons. Three lone pairs of electrons surround the sulfur atom. Sulfur has an oxidation state of +2. © UCLES 2010 9701/11/M/J/10 www.XtremePapers.net 13 34 When organic refuse decomposes in water carboxylic acids are formed. The water becomes acidic and aquatic life is destroyed. Which additives are suitable to remove this acid pollution? 1 2 3 calcium carbonate calcium hydroxide potassium nitrate 35 In a car engine, non-metallic element X forms a pollutant oxide Y. Further oxidation of Y to Z occurs in the atmosphere. In this further oxidation, 1 mol of Y reacts with ½ mol of gaseous oxygen. What can X be? 1 2 3 carbon nitrogen sulfur 36 Sulfur dioxide and sulfites are used in food preservation. Why are they used for this purpose? 1 2 3 They are reducing agents so retard the oxidation of food. They inhibit the growth of aerobic bacteria. They react with NO2(g) converting it to NO(g). 37 Propanoic acid occurs naturally as a result of the bacterial fermentation of milk, and is partly responsible for the flavour of Swiss cheese. O OH propanoic acid Which starting materials could be used to synthesise propanoic acid? 1 2 3 CH3CH2CH2OH CH3CH2CN CH3CH2CHO © UCLES 2010 9701/11/M/J/10 [Turn over www.XtremePapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 38 Which structural formulae represent 2,2-dimethylpentane? 1 2 3 (CH3)2CHCH2CH(CH3)2 (CH3)3CCH2CH2CH3 CH3CH2CH2C(CH3)3 39 Which reactions are examples of nucleophilic substitution? 1 2 3 CH3CH2Br + OH– → CH3CH2OH + Br– H+ → CH3I + H2O  CH3OH + HI CH3CH2CH2Cl + NH3 → CH3CH2CH2NH2 + HCl 40 The diagram shows some laboratory apparatus. water heat Which preparations could this apparatus be used for? 1 2 3 bromoethane, from ethanol, sodium bromide and concentrated sulfuric acid ethanal, from ethanol, sodium dichromate(VI) and sulfuric acid 1,2-dibromoethane, from bromine and ethene © UCLES 2010 9701/11/M/J/10 www.XtremePapers.net 15 BLANK PAGE © UCLES 2010 9701/11/M/J/10 www.XtremePapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2010 9701/11/M/J/10 www.XtremePapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/12 May/June 2010 1 hour *3492923324* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 13 printed pages and 3 blank pages. IB10 06_9701_12/2RP © UCLES 2010 [Turn over www.XtremePapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Which gas closely approaches ideal behaviour at room temperature and pressure? A B C D 2 ammonia carbon dioxide helium oxygen Use of the Data Booklet is relevant to this question. What could be the proton number of an element that has three unpaired electrons in each of its atoms? A 5 B 13 C 15 D 21 3 Use of the Data Booklet is relevant to this question. The elements radon (Rn), francium (Fr) and radium (Ra) have consecutive proton numbers in the Periodic Table. What is the order of their first ionisation energies? least endothermic A B C D Fr Fr Ra Rn Ra Rn Fr Ra most endothermic Rn Ra Rn Fr © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net 3 4 Some bond energy values are listed below. bond C–H C–Cl Cl–Cl Br–Br bond energy / kJ mol–1 410 340 244 193 These bond energy values relate to the following four reactions. P Q R S Br2 → 2Br 2Cl → Cl2 CH3 + Cl → CH3Cl CH4 → CH3 + H What is the order of enthalpy changes of these reactions from most negative to most positive? A B C D 5 P→Q→R→S Q→R→S→P R→Q→P→S S→P→Q→R Given the following enthalpy changes, I2(g) + 3Cl2(g) → 2ICl3(s) I2(s) → I2(g) ∆Ho = –214 kJ mol–1 ∆Ho = +38 kJ mol–1 What is the standard enthalpy change of formation of iodine trichloride, ICl3(s)? A B C D 6 +176 kJ mol–1 –88 kJ mol–1 –176 kJ mol–1 –214 kJ mol–1 Ammonium nitrate, NH4NO3, can decompose explosively when heated. NH4NO3 → N2O + 2H2O What are the changes in the oxidation numbers of the two nitrogen atoms in NH4NO3 when this reaction proceeds? A –2, –4 B +2, +6 C +4, –6 D +4, –4 © UCLES 2010 9701/12/M/J/10 [Turn over www.XtremePapers.net 4 7 Which mass of gas would occupy a volume of 3 dm3 at 25 °C and 1 atmosphere pressure? [1 mol of gas occupies 24 dm3 at 25 °C and 1 atmosphere pressure.] A B C D 8 3.2 g O2 gas 5.6 g N2 gas 8.0 g SO2 gas 11.0 g CO2 gas Use of the Data Booklet is relevant to this question. 2.920 g of a Group II metal, X, reacts with an excess of chlorine to form 5.287 g of a compound with formula XCl2. What is metal X? A B C D barium calcium magnesium strontium 9 The table gives the concentrations and pH values of the aqueous solutions of two compounds, X and Y. Either compound could be an acid or a base. X concentration pH Student P concluded that X is a strong acid. Student Q concluded that the extent of dissociation is lower in X(aq) than in Y(aq). Which of the students are correct? A B C D both P and Q neither P nor Q P only Q only 2 mol dm–3 6 Y 2 mol dm–3 9 © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net 5 10 The Haber process for the manufacture of ammonia is represented by the following equation. N2(g) + 3H2(g) 2NH3(g) ∆H = –92 kJ mol–1 Which statement is correct about this reaction when the temperature is increased? A B C D Both forward and backward rates increase. The backward rate only increases. The forward rate only increases. There is no effect on the backward or forward rate. 11 The percentage of ammonia obtainable, if equilibrium were established during the Haber process, is plotted against the operating pressure for two temperatures, 400 °C and 500 °C. Which diagram correctly represents the two graphs? A 40 % NH3 at 20 equilibrium 400 °C 500 °C 40 % NH3 at 20 equilibrium B 500 °C 400 °C 0 0 10 20 pressure / 103 kPa 0 0 10 20 pressure / 103 kPa C 40 400 °C % NH3 at 20 equilibrium 500 °C 0 0 10 20 pressure / 103 kPa % NH3 at 20 equilibrium 40 D 500 °C 400 °C 0 0 10 20 pressure / 103 kPa © UCLES 2010 9701/12/M/J/10 [Turn over www.XtremePapers.net 6 12 Swimming pool water can be kept free of harmful bacteria by adding aqueous sodium chlorate(I), NaOCl. This reacts with water to produce HOCl molecules which kill bacteria. OCl –(aq) + H2O OH–(aq) + HOCl (aq) In bright sunshine, the OCl – ion is broken down by ultra-violet light. OCl –(aq) + uv light → Cl –(aq) + ½O2(g) Which method would maintain the highest concentration of HOCl (aq)? A B C D acidify the pool water add a solution of chloride ions add a solution of hydroxide ions bubble air through the water 13 Na2S2O3 reacts with dilute HCl to give a pale yellow precipitate. If 1 cm3 of 0.1 mol dm–3 HCl is added to 10 cm3 of 0.02 mol dm–3 Na2S2O3 the precipitate forms slowly. If the experiment is repeated with 1 cm3 of 0.1 mol dm–3 HCl and 10 cm3 of 0.05 mol dm–3 Na2S2O3 the precipitate forms more quickly. Why is this? A B C D The activation energy of the reaction is lower when 0.05 mol dm–3 Na2S2O3 is used. The reaction proceeds by a different pathway when 0.05 mol dm–3 Na2S2O3 is used. The collisions between reactant particles are more violent when 0.05 mol dm–3 Na2S2O3 is used. The reactant particles collide more frequently when 0.05 mol dm–3 Na2S2O3 is used. 14 How does concentrated sulfuric acid behave when it reacts with sodium chloride? A B C D as an acid only as an acid and oxidising agent as an oxidising agent only as a reducing agent only © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net 7 15 X is a salt of one of the halogens chlorine, bromine, iodine, or astatine (proton number 85). The reaction scheme shows a series of reactions using a solution of X as the starting reagent. X HNO3(aq) AgNO3(aq) a precipitate an excess of dilute NH3(aq) a colourless solution an excess of HNO3(aq) a precipitate What could X be? A B C D sodium chloride sodium bromide potassium iodide potassium astatide 16 Which element of the third period requires the least number of moles of oxygen for the complete combustion of 1 mol of the element? A B C D aluminium magnesium phosphorus sodium 17 Two properties of non-metallic elements and their atoms are as follows. property 1 property 2 has an oxide that can form a strong acid in water has no paired 3p electrons Which properties do phosphorus and sulfur have? phosphorus A B C D 1 and 2 1 only 1 and 2 2 only sulfur 1 only 1 and 2 1 and 2 1 only © UCLES 2010 9701/12/M/J/10 [Turn over www.XtremePapers.net 8 18 Consecutive elements X, Y, Z are in the third period of the Periodic Table. Element Y has the highest first ionisation energy and the lowest melting point. What could be the identities of X, Y and Z? A B C D aluminium, silicon, phosphorus magnesium, aluminium, silicon silicon, phosphorus, sulfur sodium, magnesium, aluminium 19 Which property of Group II elements (beryllium to barium) decreases with increasing atomic number? A B C D reactivity with water second ionisation energy solubility of hydroxides stability of the carbonates 20 When gaseous chemicals are transported by road or by rail they are classified as follows. flammable non-flammable poisonous Which commonly transported gas is non-flammable? A B C D butane hydrogen oxygen propene with the two isomeric alcohols, (CH3)3CCH2OH and 21 What will react differently (CH3)2CHCH2CH2OH? A B C D acidified aqueous potassium manganate(VII) concentrated sulfuric acid phosphorus pentachloride sodium © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net 9 22 Which reagent will give similar results with both butanone and butanal? A B C D acidified aqueous potassium dichromate(VI) an alkaline solution containing complexed Cu2+ ions (Fehling’s solution) an aqueous solution containing [Ag(NH3)2]+ (Tollens’ reagent) 2,4-dinitrophenylhydrazine reagent 23 What is formed when propanone is refluxed with a solution of NaBH4? A B C D propanal propan-1-ol propan-2-ol propane 24 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D − C3H7CO 2 Na + 25 When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical substitution. In a propagation step the free radical X• is formed. CH3 CH3CH2 C CH3 CH3 + Cl ● → X● + HCl How many different forms of X• are possible? A 1 B 2 C 3 D 4 26 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration of OH– ions present. Which is the most likely molecular structure of Y? A B C D CH3CH2CH2CH2Br CH3CH2CHBrCH3 (CH3)2CHCH2Br (CH3)3CBr © UCLES 2010 9701/12/M/J/10 [Turn over www.XtremePapers.net 10 27 Which isomer of C4H10O forms three alkenes on dehydration? A B C D butan-1-ol butan-2-ol 2-methylpropan-1-ol 2-methylpropan-2-ol 28 Which compound exhibits both cis-trans and optical isomerism? A B C D CH3CH=CHCH2CH3 CH3CHBrCH=CH2 CH3CBr=CBrCH3 CH3CH2CHBrCH=CHBr 29 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated? A B C D It destroys the ozone layer. It does not burn easily. It is easily biodegradable. Its combustion products are harmful. 30 Polymerisation of 1,1-dichloroethene produces a dense, high melting point substance that does not allow gases to pass through. It is used as cling wrapping. Which sequence appears in a short length of the polymer chain? A B C D [ CH2CCl2CH2CCl2CH2CCl2 ] [ CHClCHClCHClCHClCHClCHCl ] [ CCl2CCl2CCl2CCl2CCl2CCl2 ] [ CH2CCl2CHClCHClCH2CCl2 ] © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Sodium hydrogensulfide, NaSH, is used to remove hair from animal hides. Which statements about the SH– ion are correct? 1 2 3 It contains 18 electrons. Three lone pairs of electrons surround the sulfur atom. Sulfur has an oxidation state of +2. 32 Which diagrams represent part of a giant molecular structure? 1 =C 2 =C 3 = Na = Cl 33 Which reactions are redox reactions? 1 2 3 CaBr2 + 2H2SO4 → CaSO4 + Br2 + SO2 + 2H2O CaBr2 + 2H3PO4 → Ca(H2PO4)2 + 2HBr CaBr2 + 2AgNO3 → Ca(NO3)2 + 2AgBr © UCLES 2010 9701/12/M/J/10 [Turn over www.XtremePapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 34 When organic refuse decomposes in water carboxylic acids are formed. The water becomes acidic and aquatic life is destroyed. Which additives are suitable to remove this acid pollution? 1 2 3 calcium carbonate calcium hydroxide potassium nitrate 35 In a car engine, non-metallic element X forms a pollutant oxide Y. Further oxidation of Y to Z occurs in the atmosphere. In this further oxidation, 1 mol of Y reacts with ½ mol of gaseous oxygen. What can X be? 1 2 3 carbon nitrogen sulfur 36 Sulfur dioxide and sulfites are used in food preservation. Why are they used for this purpose? 1 2 3 They are reducing agents so retard the oxidation of food. They inhibit the growth of aerobic bacteria. They react with NO2(g) converting it to NO(g). 37 Which reactions are examples of nucleophilic substitution? 1 2 3 CH3CH2Br + OH– → CH3CH2OH + Br– H+ CH3I + H2O  CH3OH + HI → CH3CH2CH2Cl + NH3 → CH3CH2CH2NH2 + HCl © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net 13 38 Propanoic acid occurs naturally as a result of the bacterial fermentation of milk, and is partly responsible for the flavour of Swiss cheese. O OH propanoic acid Which starting materials could be used to synthesise propanoic acid? 1 2 3 CH3CH2CH2OH CH3CH2CN CH3CH2CHO 39 Which structural formulae represent 2,2-dimethylpentane? 1 2 3 (CH3)2CHCH2CH(CH3)2 (CH3)3CCH2CH2CH3 CH3CH2CH2C(CH3)3 40 The diagram shows some laboratory apparatus. water heat Which preparations could this apparatus be used for? 1 2 3 bromoethane, from ethanol, sodium bromide and concentrated sulfuric acid ethanal, from ethanol, sodium dichromate(VI) and sulfuric acid 1,2-dibromoethane, from bromine and ethene © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net 14 BLANK PAGE © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net 15 BLANK PAGE © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2010 9701/12/M/J/10 www.XtremePapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/13 May/June 2010 1 hour *2288633369* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 13 printed pages and 3 blank pages. IB10 06_9701_13/RP © UCLES 2010 [Turn over www.XtremePapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Which gas closely approaches ideal behaviour at room temperature and pressure? A B C D 2 ammonia carbon dioxide helium oxygen Use of the Data Booklet is relevant to this question. The elements radon (Rn), francium (Fr) and radium (Ra) have consecutive proton numbers in the Periodic Table. What is the order of their first ionisation energies? least endothermic A B C D Fr Fr Ra Rn Ra Rn Fr Ra most endothermic Rn Ra Rn Fr 3 Use of the Data Booklet is relevant to this question. What could be the proton number of an element that has three unpaired electrons in each of its atoms? A 5 B 13 C 15 D 21 4 Given the following enthalpy changes, I2(g) + 3Cl2(g) → 2ICl3(s) I2(s) → I2(g) ∆Ho = –214 kJ mol–1 ∆Ho = +38 kJ mol–1 What is the standard enthalpy change of formation of iodine trichloride, ICl3(s)? A B C D +176 kJ mol–1 –88 kJ mol–1 –176 kJ mol–1 –214 kJ mol–1 9701/13/M/J/10 © UCLES 2010 www.XtremePapers.net 3 5 Some bond energy values are listed below. bond C–H C–Cl Cl–Cl Br–Br bond energy / kJ mol–1 410 340 244 193 These bond energy values relate to the following four reactions. P Q R S Br2 → 2Br 2Cl → Cl2 CH3 + Cl → CH3Cl CH4 → CH3 + H What is the order of enthalpy changes of these reactions from most negative to most positive? A B C D 6 P→Q→R→S Q→R→S→P R→Q→P→S S→P→Q→R Which mass of gas would occupy a volume of 3 dm3 at 25 °C and 1 atmosphere pressure? [1 mol of gas occupies 24 dm3 at 25 °C and 1 atmosphere pressure.] A B C D 3.2 g O2 gas 5.6 g N2 gas 8.0 g SO2 gas 11.0 g CO2 gas 7 Ammonium nitrate, NH4NO3, can decompose explosively when heated. NH4NO3 → N2O + 2H2O What are the changes in the oxidation numbers of the two nitrogen atoms in NH4NO3 when this reaction proceeds? A –2, –4 B +2, +6 C +4, –6 D +4, –4 © UCLES 2010 9701/13/M/J/10 [Turn over www.XtremePapers.net 4 8 The Haber process for the manufacture of ammonia is represented by the following equation. N2(g) + 3H2(g) 2NH3(g) ∆H = –92 kJ mol–1 Which statement is correct about this reaction when the temperature is increased? A B C D 9 Both forward and backward rates increase. The backward rate only increases. The forward rate only increases. There is no effect on the backward or forward rate. Use of the Data Booklet is relevant to this question. 2.920 g of a Group II metal, X, reacts with an excess of chlorine to form 5.287 g of a compound with formula XCl2. What is metal X? A B C D barium calcium magnesium strontium 10 The table gives the concentrations and pH values of the aqueous solutions of two compounds, X and Y. Either compound could be an acid or a base. X concentration pH Student P concluded that X is a strong acid. Student Q concluded that the extent of dissociation is lower in X(aq) than in Y(aq). Which of the students are correct? A B C D both P and Q neither P nor Q P only Q only 2 mol dm–3 6 Y 2 mol dm–3 9 © UCLES 2010 9701/13/M/J/10 www.XtremePapers.net 5 11 How does concentrated sulfuric acid behave when it reacts with sodium chloride? A B C D as an acid only as an acid and oxidising agent as an oxidising agent only as a reducing agent only 12 Swimming pool water can be kept free of harmful bacteria by adding aqueous sodium chlorate(I), NaOCl. This reacts with water to produce HOCl molecules which kill bacteria. OCl –(aq) + H2O OH–(aq) + HOCl (aq) In bright sunshine, the OCl – ion is broken down by ultra-violet light. OCl –(aq) + uv light → Cl –(aq) + ½O2(g) Which method would maintain the highest concentration of HOCl (aq)? A B C D acidify the pool water add a solution of chloride ions add a solution of hydroxide ions bubble air through the water 13 Na2S2O3 reacts with dilute HCl to give a pale yellow precipitate. If 1 cm3 of 0.1 mol dm–3 HCl is added to 10 cm3 of 0.02 mol dm–3 Na2S2O3 the precipitate forms slowly. If the experiment is repeated with 1 cm3 of 0.1 mol dm–3 HCl and 10 cm3 of 0.05 mol dm–3 Na2S2O3 the precipitate forms more quickly. Why is this? A B C D The activation energy of the reaction is lower when 0.05 mol dm–3 Na2S2O3 is used. The reaction proceeds by a different pathway when 0.05 mol dm–3 Na2S2O3 is used. The collisions between reactant particles are more violent when 0.05 mol dm–3 Na2S2O3 is used. The reactant particles collide more frequently when 0.05 mol dm–3 Na2S2O3 is used. © UCLES 2010 9701/13/M/J/10 [Turn over www.XtremePapers.net 6 14 X is a salt of one of the halogens chlorine, bromine, iodine, or astatine (proton number 85). The reaction scheme shows a series of reactions using a solution of X as the starting reagent. X HNO3(aq) AgNO3(aq) a precipitate an excess of dilute NH3(aq) a colourless solution an excess of HNO3(aq) a precipitate What could X be? A B C D sodium chloride sodium bromide potassium iodide potassium astatide 15 The percentage of ammonia obtainable, if equilibrium were established during the Haber process, is plotted against the operating pressure for two temperatures, 400 °C and 500 °C. Which diagram correctly represents the two graphs? A 40 % NH3 at 20 equilibrium 400 °C 500 °C 40 % NH3 at 20 equilibrium B 500 °C 400 °C 0 0 10 20 pressure / 103 kPa 0 0 10 20 pressure / 103 kPa C 40 % NH3 at 20 equilibrium 500 °C 0 0 10 20 pressure / 103 kPa 400 °C 40 % NH3 at 20 equilibrium D 500 °C 400 °C 0 0 10 20 pressure / 103 kPa © UCLES 2010 9701/13/M/J/10 www.XtremePapers.net 7 16 Two properties of non-metallic elements and their atoms are as follows. property 1 property 2 has an oxide that can form a strong acid in water has no paired 3p electrons Which properties do phosphorus and sulfur have? phosphorus A B C D 1 and 2 1 only 1 and 2 2 only sulfur 1 only 1 and 2 1 and 2 1 only 17 Consecutive elements X, Y, Z are in the third period of the Periodic Table. Element Y has the highest first ionisation energy and the lowest melting point. What could be the identities of X, Y and Z? A B C D aluminium, silicon, phosphorus magnesium, aluminium, silicon silicon, phosphorus, sulfur sodium, magnesium, aluminium 18 Which property of Group II elements (beryllium to barium) decreases with increasing atomic number? A B C D reactivity with water second ionisation energy solubility of hydroxides stability of the carbonates 19 Which element of the third period requires the least number of moles of oxygen for the complete combustion of 1 mol of the element? A B C D aluminium magnesium phosphorus sodium © UCLES 2010 9701/13/M/J/10 [Turn over www.XtremePapers.net 8 20 When gaseous chemicals are transported by road or by rail they are classified as follows. flammable non-flammable poisonous Which commonly transported gas is non-flammable? A B C D butane hydrogen oxygen propene with the two isomeric alcohols, (CH3)3CCH2OH and 21 What will react differently (CH3)2CHCH2CH2OH? A B C D acidified aqueous potassium manganate(VII) concentrated sulfuric acid phosphorus pentachloride sodium 22 What is formed when propanone is refluxed with a solution of NaBH4? A B C D propanal propan-1-ol propan-2-ol propane 23 When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical substitution. In a propagation step the free radical X• is formed. CH3 CH3CH2 C CH3 CH3 + Cl ● → X● + HCl How many different forms of X• are possible? A 1 B 2 C 3 D 4 © UCLES 2010 9701/13/M/J/10 www.XtremePapers.net 9 24 Which reagent will give similar results with both butanone and butanal? A B C D acidified aqueous potassium dichromate(VI) an alkaline solution containing complexed Cu2+ ions (Fehling’s solution) an aqueous solution containing [Ag(NH3)2]+ (Tollens’ reagent) 2,4-dinitrophenylhydrazine reagent 25 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium hydroxide? A CH3OH B C3H7OH C C3H7CO2H D − C3H7CO 2 Na + 26 Which compound exhibits both cis-trans and optical isomerism? A B C D CH3CH=CHCH2CH3 CH3CHBrCH=CH2 CH3CBr=CBrCH3 CH3CH2CHBrCH=CHBr 27 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to provide heat for power stations. Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated? A B C D It destroys the ozone layer. It does not burn easily. It is easily biodegradable. Its combustion products are harmful. 28 Polymerisation of 1,1-dichloroethene produces a dense, high melting point substance that does not allow gases to pass through. It is used as cling wrapping. Which sequence appears in a short length of the polymer chain? A B C D [ CH2CCl2CH2CCl2CH2CCl2 ] [ CHClCHClCHClCHClCHClCHCl ] [ CCl2CCl2CCl2CCl2CCl2CCl2 ] [ CH2CCl2CHClCHClCH2CCl2 ] © UCLES 2010 9701/13/M/J/10 [Turn over www.XtremePapers.net 10 29 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration of OH– ions present. Which is the most likely molecular structure of Y? A B C D CH3CH2CH2CH2Br CH3CH2CHBrCH3 (CH3)2CHCH2Br (CH3)3CBr 30 Which isomer of C4H10O forms three alkenes on dehydration? A B C D butan-1-ol butan-2-ol 2-methylpropan-1-ol 2-methylpropan-2-ol © UCLES 2010 9701/13/M/J/10 www.XtremePapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Which reactions are redox reactions? 1 2 3 CaBr2 + 2H2SO4 → CaSO4 + Br2 + SO2 + 2H2O CaBr2 + 2H3PO4 → Ca(H2PO4)2 + 2HBr CaBr2 + 2AgNO3 → Ca(NO3)2 + 2AgBr 32 Sodium hydrogensulfide, NaSH, is used to remove hair from animal hides. Which statements about the SH– ion are correct? 1 2 3 It contains 18 electrons. Three lone pairs of electrons surround the sulfur atom. Sulfur has an oxidation state of +2. 33 Which diagrams represent part of a giant molecular structure? 1 =C 2 =C 3 = Na = Cl © UCLES 2010 9701/13/M/J/10 [Turn over www.XtremePapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 34 In a car engine, non-metallic element X forms a pollutant oxide Y. Further oxidation of Y to Z occurs in the atmosphere. In this further oxidation, 1 mol of Y reacts with ½ mol of gaseous oxygen. What can X be? 1 2 3 carbon nitrogen sulfur 35 When organic refuse decomposes in water carboxylic acids are formed. The water becomes acidic and aquatic life is destroyed. Which additives are suitable to remove this acid pollution? 1 2 3 calcium carbonate calcium hydroxide potassium nitrate 36 Sulfur dioxide and sulfites are used in food preservation. Why are they used for this purpose? 1 2 3 They are reducing agents so retard the oxidation of food. They inhibit the growth of aerobic bacteria. They react with NO2(g) converting it to NO(g). 37 Which structural formulae represent 2,2-dimethylpentane? 1 2 3 (CH3)2CHCH2CH(CH3)2 (CH3)3CCH2CH2CH3 CH3CH2CH2C(CH3)3 © UCLES 2010 9701/13/M/J/10 www.XtremePapers.net 13 38 Which reactions are examples of nucleophilic substitution? 1 2 3 CH3CH2Br + OH– → CH3CH2OH + Br– H+ CH3I + H2O  CH3OH + HI → CH3CH2CH2Cl + NH3 → CH3CH2CH2NH2 + HCl 39 Propanoic acid occurs naturally as a result of the bacterial fermentation of milk, and is partly responsible for the flavour of Swiss cheese. O OH propanoic acid Which starting materials could be used to synthesise propanoic acid? 1 2 3 CH3CH2CH2OH CH3CH2CN CH3CH2CHO 40 The diagram shows some laboratory apparatus. water heat Which preparations could this apparatus be used for? 1 2 3 bromoethane, from ethanol, sodium bromide and concentrated sulfuric acid ethanal, from ethanol, sodium dichromate(VI) and sulfuric acid 1,2-dibromoethane, from bromine and ethene © UCLES 2010 9701/13/M/J/10 www.XtremePapers.net 14 BLANK PAGE © UCLES 2010 9701/13/M/J/10 www.XtremePapers.net 15 BLANK PAGE © UCLES 2010 9701/13/M/J/10 www.XtremePapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2010 9701/13/M/J/10 www.XtremePapers.net CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY PAPER 1 Multiple Choice 9701/1 OCTOBER/NOVEMBER SESSION 2002 1 hour Candidates answer on the question paper. Additional materials: Multiple Choice answer sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet TIME 1 hour INSTRUCTIONS TO CANDIDATES Do not open this booklet until you are told to do so. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has already been done for you. There are forty questions in this paper. Answer all questions. For each question, there are four possible answers, A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read very carefully the instructions on the answer sheet. INFORMATION FOR CANDIDATES Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This question paper consists of 13 printed pages and 3 blank pages. SP (SC/KN) S17937/3 © CIE 2002 [Turn over www.xtremepapers.net 2 Section A For each question, there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 A mixture of 10 cm3 of methane and 10 cm3 of ethane was sparked with an excess of oxygen. After cooling to room temperature, the residual gas was passed through aqueous potassium hydroxide. What volume of gas was absorbed by the alkali? A B C D 15 cm3 20 cm3 30 cm3 40 cm3 2 One of the most important chemical species responsible for the removal of ozone from the stratosphere is a free radical of chlorine, 35Cl •. What does 35Cl • contain? protons A B C D 17 17 18 18 neutrons 18 18 17 17 electrons 16 17 17 18 3 Use of the Data Booklet is relevant to this question. In the gas phase, aluminium and a transition element require the same amount of energy to form one mole of an ion with a 2+ charge. What is the transition element? A B C D Co Cr Cu Ni 9701/1/O/N/02 www.xtremepapers.net 3 4 The African weaver ant defends its territory by spraying an intruder with a mixture of compounds. The ease by which these compounds are detected by other ants depends upon the volatility, which decreases as the strength of the intermolecular forces in the compound increases. Which compound would be the most volatile? A B C D CH3CH2CH2CH2CH2CH3 CH3CH2CH2CH2CH2CHO CH3CH2CH2CH2CH2NH2 CH3CH2CH2CH2CH2OH 5 Which of the following molecules has no permanent dipole? A CCl2F2 B CHCl3 C C2Cl4 D C2H5Cl 6 Which is the most likely shape of a molecule of hydrazine, N2H4? H 90° A N H H 90° B H N N H N H H H H C H N 120° N H H 107° H D H N H N H 7 Which of the following exists in the solid state as a giant covalent lattice? A B C D ice iodine silicon(IV) oxide tin(IV) chloride 9701/1/O/N/02 [Turn over www.xtremepapers.net 4 8 A 2 g sample of hydrogen at temperature T and of volume V exerts a pressure p. Deuterium, 2 H, is an isotope of hydrogen. 1 Which of the following would also exert a pressure p at the same temperature T ? A B C D 2 g of deuterium of volume V _ 4 g of deuterium of volume V 2 a mixture of 1 g of hydrogen and 2 g of deuterium of total volume V a mixture of 2 g of hydrogen and 1 g of deuterium of total volume 2 V 9 The following energy cycle represents the enthalpy changes in the formation of carbon dioxide from its constituent elements in their standard states. What substances are present at level Y in this diagram? level Y 0 energy ∆Hf A B C D C(g) + 2O(g) C(g) + O2(g) C(s) + O2(g) CO2(g) 9701/1/O/N/02 www.xtremepapers.net 5 10 At 600 °C oxides of nitrogen react with unburnt hydrocarbons in a catalytic converter in a car exhaust. The equation using methane as representative of a hydrocarbon molecule would be as follows. 4NO + CH4 → 2N2 + CO2 + 2H2O Which statement is likely to be true about the energy change of this reaction? A B C D It is endothermic as heat energy is converted into chemical energy. It is exothermic as a high temperature is required. __ __ It is exothermic as the triple bond N ← O is broken. It is exothermic as the products have large negative enthalpy changes of formation. 11 In an experiment, b mol of hydrogen iodide were put into a sealed vessel under pressure p. At equilibrium, x mol of the hydrogen iodide had dissociated, the reaction being represented by the following equation. 2HI(g) H2(g) + I2(g) Which expression for Kp is correct? A x2 ______ (b – x)2 x 2 p2 ______ (b – x)2 x 2 p2 _______ 4b(b – x) x2 ______ 4(b – x)2 B C D 12 A piece of zinc foil dissolved completely in 20 cm 3 of a dilute sulphuric acid solution and the volume of hydrogen evolved was noted at equal, short time intervals. Another piece of zinc foil of the same surface area and mass was added to 40 cm 3 of the same solution of dilute sulphuric acid. How will the initial rate of reaction and the total volume of hydrogen evolved in this second experiment compare to the first experiment? initial rate of reaction A B C D no change no change increase increase total volume of hydrogen evolved decrease no change no change increase 9701/1/O/N/02 [Turn over www.xtremepapers.net 6 13 The chloride of element Q is hydrolysed by water to form an acidic solution and its oxide reacts with acid to form a salt. What could be the element Q? A B C D magnesium aluminium silicon phosphorus 14 Which diagram represents the change in ionic radius of the elements across the third period (Na to Cl)? A B C D Na Cl Na Cl Na Cl Na Cl 15 The propellant used in the solid rocket booster of a space shuttle is a mixture of aluminium and compound X. Compound X contains chlorine in an oxidation state of +7. Which of the following could be compound X? A NH4Cl B NH4ClO3 C NH4ClO4 D N2H5Cl 16 River water in a chalky agricultural area may contain Ca2+, Mg2+, CO2–, HCO– , Cl–, and NO– 3 3 3 ions. In a waterworks, such water is treated by adding a calculated quantity of calcium hydroxide. What will be precipitated following the addition of calcium hydroxide? A B C D CaCl2 CaCO3 MgCO3 Mg(NO3)2 9701/1/O/N/02 www.xtremepapers.net 7 17 The standard enthalpy changes of formation of HCl and HI are –92 kJ mol–1 and +26 kJ mol–1 respectively. Which statement is most important in explaining this difference? A B C D Chlorine is more electronegative than iodine. The activation energy for the H2/Cl2 reaction is much less than that for the H2/I2 reaction. The bond energy of HI is smaller than the bond energy of HCl. The bond energy of I2 is smaller than the bond energy of Cl2. 18 In the industrial electrolysis of brine to manufacture chlorine, the diaphragm used is a porous screen which allows the flow of electrolytes but keeps other chemicals separate. Which substance needs to be kept separate from the chlorine by the diaphragm? A B C D hydrogen sodium hydroxide sodium chloride water 19 Which gas is present in the exhaust fumes of a car engine in a much greater amount than any other gas? A B C D carbon dioxide carbon monoxide nitrogen water vapour 20 The Russian composer Borodin was also a research chemist who discovered a reaction in which two ethanal molecules combine to form a compound commonly known as aldol (reaction I). Aldol forms another compound on heating (reaction II). I 2CH3CHO → CH3CH(OH)CH2CHO II CH3CH(OH)CH2CHO → CH3CH=CHCHO + H2O Which of the following best describes reactions I and II? I A B C D addition addition elimination substitution II elimination reduction reduction elimination 9701/1/O/N/02 [Turn over www.xtremepapers.net 8 21 Camphor is used for medical purposes, the diagram shows its structure. CH3 C CH2 CH2 C CH3 C C H How many chiral centres are present in one molecule of camphor? A 0 B 1 C 2 D 3 CH3 CH2 O 22 Chloroethane is used as a starting material for the production of ‘time-release capsules’ in pharmaceutical products. One way of preparing chloroethane is to react chlorine and ethane in the presence of ultraviolet light. Which statement is correct about the first stage of the mechanism of this reaction? A B C D The Cl – Cl bond is split homolytically. The Cl – Cl bond is split heterolytically. The C – H bond is split homolytically. The C – H bond is split heterolytically. 23 Chloroethene, CH2=CHCl, is the monomer of pvc. What are the C–C–C bond angles along the polymeric chain in pvc? A B C D They are all 109 °. Half are 109 ° and half are 120 °. They are all 120 °. They are all 180 °. 9701/1/O/N/02 www.xtremepapers.net 9 24 Compound X undergoes the following reactions. NaOH(aq) / heat Cr2O2–, H+(aq) / heat 7 C4H9Br → C4H10O → C4H8O only X What is X? A B C D 1-bromobutane 2-bromobutane 1-bromo-2-methylpropane 2-bromo-2-methylpropane 25 Chlorofluorocarbons (CFCs) have been widely used in aerosol sprays, refrigerators and in making foamed plastics, but are now known to destroy ozone in the upper atmosphere. Which of the following will not destroy ozone, and therefore can be used safely as a replacement for CFCs? A CHBr3 B CCl3CBr3 C CHClFCClF2 D CH3CH2CH2CH3 26 Oxidation of an alkene Y gives a diol; further oxidation gives a diketone. What could be Y? A B C D CH3CH=C(CH3)2 (CH3)2CHCH=CH2 C6H5CH=CHC6H5 (C6H5)2C=CHCH3 27 Burnt sugar has a characteristic smell caused partly by the following compound. It has two functional groups indicated by Q and R. Q CH3 O C CHO R When this compound is tested in a laboratory with 2,4-dinitrophenylhydrazine and Fehling’s reagent, which functional groups are responsible for positive tests? 2,4-dinitrophenylhydazine A B C D Q and R R only Q and R Q only Fehling’s reagent Q and R Q and R R only R only 9701/1/O/N/02 [Turn over www.xtremepapers.net 10 28 Ethanal may be converted into a three-carbon acid in a two-step process. Which compound is the intermediate? A CH3CO2H B CH3CN C CH3CH2CN D CH3CH(OH)CN 29 Which compound is both chiral and acidic? A H C C H B CH3 CO2H OH CO2H CH2Br C HCO2CH CH3 D CH(OH)CO2H CH2CO2H 9701/1/O/N/02 www.xtremepapers.net 11 30 An ester with an odour of banana has the following formula. CH3CO2CH2CHCH2CH3 CH3 In which of the following do the substances react together, under suitable conditions, to produce this ester? A CH3CH2CHCH2CO2H + CH3OH CH3 B CH3CH2CHCO2H + CH3CH2OH CH3 C CH3CO2H + CH3CH2CHCH2OH CH3 D CH3CO2H + CH3CH2CHCH2OH CH3 9701/1/O/N/02 [Turn over www.xtremepapers.net 12 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Which compounds have the empirical formula CH2O? 1 2 3 methanal ethanoic acid methyl methanoate 32 Which of the following are features of the structure of metallic copper? 1 2 3 ionic bonds delocalised electrons lattice of ions 33 Which statements about the commercial extraction of aluminium are correct? 1 2 3 The cathode reaction is Al 3+ + 3e– → Al. The lining of the electrolytic cell acts as the cathode. The electrolyte is purified Al2O3 in Na3AlF6. 34 Which of the following magnesium compounds lose mass when heated by a bunsen flame? 1 2 3 magnesium carbonate magnesium nitrate magnesium oxide 9701/1/O/N/02 www.xtremepapers.net 13 35 The element astatine lies below iodine in Group VII of the Periodic Table. What will be the properties of astatine? 1 2 3 It forms diatomic molecules which dissociate more readily than chlorine molecules. It reacts explosively with hydrogen. It is a good reducing agent. 36 Ammonia and chlorine react in the gas phase. 8NH3 + 3Cl2 → N2 + 6NH4Cl Which statements are correct? 1 2 3 Ammonia behaves as a reducing agent. Ammonia behaves as a base. The oxidation number of the hydrogen changes. 37 Which compounds show cis-trans isomerism? 1 2 3 but-2-ene but-1-ene 2-methylpropene 38 When octane is subjected to catalytic cracking, which compounds can be obtained? 1 2 3 CH2=CH2 CH3CH2CH=CH2 CH3(CH2)4CH3 39 Which ions are present in a solution of ethanol in an excess of concentrated sulphuric acid? 1 2 3 CH3CH2O– + CH3CH2OH2 HSO– 4 40 In the reaction between an aldehyde and HCN catalysed by NaCN, which statements about the reaction mechanism are true? 1 2 3 A new carbon-carbon bond is formed. In the intermediate, the oxygen carried a negative charge. The last stage involves the formation of a hydrogen-oxygen bond. 9701/1/O/N/02 www.xtremepapers.net 14 BLANK PAGE 9701/1/O/N/02 www.xtremepapers.net 15 BLANK PAGE 9701/1/O/N/02 www.xtremepapers.net 16 BLANK PAGE 9701/1/O/N/02 www.xtremepapers.net CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice October/November 2003 1 hour Additional Materials: Data Booklet Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) 9701/01 READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C, and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 14 printed pages and 2 blank pages. SP (NF/KN) S34065/4 © UCLES 2003 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Use of the Data Booklet is relevant to this question. Analytical chemists can detect very small amounts of amino acids, down to 3 × 10–21 mol. How many molecules of an amino acid (Mr = 200) would this be? A 9 B 200 C 1800 D 360 000 2 Use of the Data Booklet is relevant to this question. A garden fertiliser is said to have a phosphorus content of 30.0 % ‘P2O5 soluble in water’. What is the percentage by mass of phosphorus in the fertiliser? A 6.55 % B 13.1 % C 26.2 % D 30.0 % 3 A sample of the hydrocarbon C6H12 is completely burned in dry oxygen and the product gases are collected as shown. [Ar : H, 1 ; C, 12 ; O, 16.] H2O + CO2 + excess of O2 excess of O2 P Q anhydrous calcium chloride (to absorb H2O) sodalime (to absorb CO2) The increases in mass of the collecting vessels P and Q of the apparatus are MP and MQ, respectively. What is the ratio MP / MQ? A 0.41 B 0.82 C 1.2 D 2.4 9701/1/O/N/03 www.xtremepapers.net 3 4 Unnilpentium is an artificial element. One of its isotopes is 262Unp. 105 Which of the following statements is correct? A B C D 262Unp 105 has a nucleon number of 105. The atom 260X is an isotope of 262Unp. 105 105 There are 262 neutrons in 262Unp. 105 The proton number of 262Unp is 262. 105 5 The table gives the successive ionisation energies for an element X. 1st ionisation energy / kJ mol–1 950 2nd 1800 3rd 2700 4th 4800 5th 6000 6th 12300 What could be the formula of the chloride of X ? A XCl B XCl2 C XCl3 D XCl4 6 Which molecule contains only six bonding electrons? A C2H4 B C2F6 C H2O D NF3 7 Chemists have been interested in the properties of hydrogen selenide, H2Se, to compare it with ‘bad egg’ gas hydrogen sulphide, H2S. Which set of data would the hydrogen selenide molecule be expected to have? number of lone pairs on Se atom A B C D 1 2 2 2 bond angle 104 ° 104 ° 109 ° 180 ° 9701/1/O/N/03 [Turn over www.xtremepapers.net 4 8 A substance commonly found in the house or garden has the following properties. • • • It is combustible. It is an electrical insulator. It melts over a range of temperature. What could the substance be? A B C D brass paper poly(ethene) silicon(IV) oxide 9 Use of the Data Booklet is relevant to this question. In an experiment using a gas syringe, 0.10 g of a gas is found to occupy 83.1 cm3, measured at standard pressure (1.0 × 105 Pa) and 27 °C. What is the relative molecular mass of the gas? A B C D 0.10 × 8.31 × 27 1.0 × 105 × 83.1 0.10 × 8.31 × 300 1.0 × 105 × 83.1 0.10 × 8.31 × 27 1.0 × 105 × 83.1 × 10–6 0.10 × 8.31 × 300 1.0 × 105 × 83.1 × 10–6 9701/1/O/N/03 www.xtremepapers.net 5 10 The value of pV is plotted against p for two gases, an ideal gas and a non-ideal gas, where p is the pressure and V is the volume of the gas. pV non-ideal gas ideal gas 0 0 p Which of the following gases shows the greatest deviation from ideality? A B C D ammonia ethene methane nitrogen 11 The ‘flash’ produced by nineteenth century photographers to take indoor photographs was obtained from the following reaction. 3Mg + KClO3 → 3MgO + KCl The standard enthalpy changes of formation are given below. ∆H fo / kJ mol–1 MgO KCl KClO3 –602 –437 –391 _ What is the standard enthalpy change of the ‘flash’ reaction? A B C D –3(–602) + (–437) – (–391) (–602) + (–437) – (–391) 3(–602) + (–437) – (–391) (–602) + 3(–437) – 3(–391) 9701/1/O/N/03 [Turn over www.xtremepapers.net 6 12 Why does the exothermic reaction C(diamond) → C(graphite) not occur spontaneously? A B C D A tetrahedral configuration is always more stable than a planar one. Diamond has only strong covalent bonds whereas graphite has both covalent bonds and van der Waals’ forces. The change from diamond to graphite has a high activation energy. The density of graphite is less than that of diamond. ∆H = –3 kJ mol–1 13 The sketch below shows the variation of first ionisation energy with proton number for six elements of consecutive proton numbers between 1 and 18 (H to Ar). ionisation energy X proton number What is the identity of the element X? A Mg B Al C Si D P 14 The metals of Group II react readily with oxygen to form compounds of general formula MO. When each of these oxides is added to water, which forms the most alkaline solution? A MgO B CaO C SrO D BaO 15 One mole of each of the following compounds is strongly heated and any gas produced is collected at room temperature and pressure. From which compound is 24 dm3 of gas likely to be collected? [One mole of any gas occupies 24 dm3 at room temperature and pressure.] A MgCl2 B MgCO3 C Mg(NO3)2 D Mg(OH)2 9701/1/O/N/03 www.xtremepapers.net 7 16 In black and white photographic film, light converts silver chloride into metallic silver. After the film has been developed, the unexposed silver chloride is removed by reaction with sodium thiosulphate to produce a ‘fixed’ negative. AgCl + 2Na2S2O3 → 4Na+ + Cl – + [Ag(S2O3)2]3– What is the function of thiosulphate? A B C D to make the silver ions soluble to oxidise the silver ions to oxidise the silver metal to reduce silver ions 17 In what order does the reducing power of the hydrogen halides increase? A B C D HCl, HBr, HI HCl, HI, HBr HBr, HI, HCl HI, HBr, HCl 18 In a solution of ammonia in water, what combination of ionic and molecular forms of ammonia are present? A B C D ions only ions and simple molecules only simple molecules and hydrogen-bonded molecules only simple molecules, hydrogen–bonded molecules and ions 19 Nitrogen is frequently used as an inert atmosphere because it is an unreactive gas. Which is the best explanation of this unreactivity? A B C D Its molecule contains a triple bond. The bond energy of the molecule is high (994 kJ mol–1). The bond in its molecule is very short (0.110 nm). The three p orbitals of nitrogen are half-filled. 20 How many alcohols (including both structural isomers and stereoisomers) can have the molecular formula C4H10O? A 3 B 4 C 5 D 6 9701/1/O/N/03 [Turn over www.xtremepapers.net 8 21 Hydrogen bromide reacts with ethene to form bromoethane. What is the best description of the organic intermediate in this reaction? A B C D It contains carbon, hydrogen and bromine. It has a negative charge. It is an electrophile. It is a free radical. 22 On strong heating a hydrocarbon produces ethene, propane and but-1-ene in the mole ratio 5 : 1 : 1. What is the molecular formula of the hydrocarbon? A C17H34 B C17H36 C C19H38 D C19H40 23 1,2-Dibromo-3-chloropropane (DBCP) has been used in the control of earthworms in agricultural land. What would be the best synthesis of this compound? A B C D CH3CH2CH2Cl + 2Br2 → DBCP + 2HBr CH3CHBrCH2Br + Cl2 → DBCP + HCl CH2=CHCH2Cl + Br2 → DBCP ClCH2CH=CH2 + PBr5 → DBCP + PBr3 24 Each of the following compounds is effective as a refrigerant. The release of which one of these causes the greatest depletion of the ozone layer? A CCl2F2 B CH3OCH3 C CH3CHF2 D CH3CH2CH3 25 1,1-Dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal. NaOH(aq) CH3CH2CHCl2 → CH3CH2CHO What is the mechanism of the first step of this reaction? A B C D electrophilic substitution elimination nucleophilic substitution oxidation 9701/1/O/N/03 www.xtremepapers.net 9 26 Which alcohol gives only one oxidation product when warmed with dilute acidified potassium dichromate(VI)? A B C D butan-1-ol butan-2-ol 2-methylpropan-1-ol 2-methylpropan-2-ol 27 What will react differently (CH3)2CHCH2CH2OH? A B C D with the two isomeric pentanols, (CH3)3CCH2OH and acidified aqueous potassium manganate(VII) concentrated sulphuric acid phosphorus pentachloride sodium 28 How many hydrogen atoms in a molecule of glycerol, HOCH2CH(OH)CH2OH, may be substituted by deuterium on dissolving it in an excess of D2O? A 2 B 3 C 5 D 8 29 CH3CH2COCH2CH3 reacts with hydrogen cyanide to form a cyanohydrin. Which features apply to the product? A B C D It has one chiral centre. It is formed by electrophilic addition. It is formed via a C–OH intermediate. Its formation requires the use of cyanide ions as a catalyst. 9701/1/O/N/03 [Turn over www.xtremepapers.net 10 30 A compound X has all of the properties below. • • • It is a liquid at 25 °C. It mixes completely with water. It reacts with aqueous sodium hydroxide. What could X be? A B C D ethanoic acid ethanol ethene ethyl ethanoate 9701/1/O/N/03 www.xtremepapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 It is suggested that the solid deposits of ammonium compounds on the leaves of trees found in areas of high pollution are caused by the following reaction. 2NH3 + SO3 + H2O → (NH4)2SO4 Which of these take place in this reaction? 1 2 3 an acid-base reaction ionic bond formation oxidation and reduction 32 One explanation of the explosion at the Chernobyl nuclear power plant in 1986 is that the graphite reactor overheated and reacted with the cooling water according to the following equation. C(s) + H2O(g) H2(g) + CO(g) ∆H = + 131 kJ mol–1 What are possible reasons why the forward reaction is more likely to occur at high temperature? 1 2 3 Hydrogen and carbon monoxide do not react at high temperature. At lower temperature, the position of equilibrium lies too far to the left. The energy of activation is high. 9701/1/O/N/03 [Turn over www.xtremepapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 33 The diagram represents the Boltzmann distribution of molecular energies at a given temperature. proportion of molecules energy As temperature increases, which statements are correct? 1 2 3 The maximum of the curve is displaced to the right. The proportion of molecules with energies above any given value increases. The proportion of molecules with any given energy increases. 34 Which statements concerning the third period elements (sodium to argon) and their compounds are correct? 1 2 3 The elements become more electronegative from sodium to chlorine. Aluminium oxide is the only oxide which is insoluble in water. The maximum oxidation state is shown by silicon. 35 A farmer spreads lime on land which has already been treated with a nitrogenous fertiliser. Which reactions will occur over a period of time? 1 2 3 Ca(OH)2 + CO2 → CaCO3 + H2O Ca(OH)2 + 2H+(aq) → Ca2+(aq) + 2H2O Ca(OH)2 + 2NH+ (aq) → Ca2+(aq) + 2NH3 + 2H2O 4 9701/1/O/N/03 www.xtremepapers.net 13 36 Which processes involve the conversion of sulphur dioxide into sulphur trioxide? 1 2 3 the combustion of sulphur contaminated carbonaceous fuels the Contact process for manufacturing sulphuric acid the catalytic oxidation of sulphur dioxide by oxides of nitrogen 37 Which molecules would be present in the photochemical chlorination of methane? 1 2 3 hydrogen hydrogen chloride dichloromethane 38 The taste buds on the tongue are chiral and can distinguish one optical isomer from another. Which naturally-occurring compounds will have optical isomers that may be distinguished by taste? CH H 1 H H C C C O OH OH OH 2 CH CH3 CH3 OH 3 HO CH3 O C CH CH O C OH CH2OH ribose menthol maleic acid 39 The compound shown is a hormone produced during pregnancy to suppress ovulation. CH3 C CH3 CH3 O O Which reagents would give positive results with this compound? 1 2 3 aqueous bromine 2,4-dinitrophenylhydrazine Fehling’s reagent 9701/1/O/N/03 [Turn over www.xtremepapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 40 The flavour of pineapples is partly due to the compound Q. O CH3CH2CH2COCH3 Q When Q is heated under reflux with NaOH(aq) and the mixture distilled, what compounds will be found in the distillate? 1 2 3 CH3OH CH3CH2CH2CO2Na CH3CH2CH2OH 9701/1/O/N/03 www.xtremepapers.net 15 BLANK PAGE 9701/1/O/N/03 www.xtremepapers.net 16 BLANK PAGE 9701/1/O/N/03 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice October/November 2004 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C, and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read the instructions on the answer sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 18 printed pages and 2 blank pages. IB04 11_9701_01/3RP  UCLES 2004 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Granular urea, CON2H4, can be used to remove NO2 from the flue gases of power stations, converting it into harmless nitrogen. 2CON2H4 + x NO2 → 2CO2 + y H2O + z N2 What are the values of x, y and z in a balanced equation? x A B C D 2 1½ 2 3 3 y 2 4 4 4 z 1¼ 3 3½ 3 The diagram shows the mass spectrum of a sample of zinc. Use the data to calculate the relative atomic mass of the sample. 100 80 60 relative abundance / % 40 20 0 64 65 Ar 66 67 A 65 B 65.25 C 65.5 D 65.66 3 The foul smell that skunks spray is due to a number of thiols, one of which is methanethiol, CH3SH, which burns as follows. CH3SH + 3O2 → CO2 + SO2 + 2H2O A sample of 10 cm3 of methanethiol was exploded with 60 cm3 of oxygen. What would be the final volume of the resultant mixture of gases when cooled to room temperature? A 20 cm3 B 30 cm3 C 50 cm3 D 70 cm3  UCLES 2004 9701/01/O/N/04 www.xtremepapers.net 3 4 Use of the Data Booklet is relevant to this question. It is now thought that where an element exists as several isotopes, the stable ones usually contain a ‘magic number’ of neutrons. One of these magic numbers is 126. Which isotope is unstable? A 209 Bi B 208 Pb C 210 Po D 208 Tl 5 An atom has eight electrons. Which diagram shows the electronic configuration of this atom in its lowest energy state? A B C D 6 The gecko, a small lizard, can climb up a smooth glass window. The gecko has millions of microscopic hairs on its toes and each hair has thousands of pads at its tip. The result is that the molecules in the pads are extremely close to the glass surface on which the gecko is climbing. What is the attraction between the gecko’s toe pads and the glass surface? A B C D co-ordinate bonds covalent bonds ionic bonds van der Waals’ forces 7 What are the bond angles in the PH3 molecule likely to be? A 90 o B 104 o C 109 o D 120 o  UCLES 2004 9701/01/O/N/04 [Turn over www.xtremepapers.net 4 8 Use of the Data Booklet is relevant to this question. Which expression gives the pressure exerted by 1.6 x 10– 3 mol of N2 in a container of volume 3.0 dm3 at 273 oC? A 1.6 x10 −3 x 8.31 x 273 3.0 x 10 − 6 1.6 x 10 − 3 x 8.31 x (273 + 273) 3.0 x 10 − 6 1.6 x 10 − 3 x 8.31 x 273 3.0 x 10 −3 1.6 x 10 − 3 x 8.31 x (273 + 273) 3.0 x 10 − 3 Pa B Pa C D Pa Pa 9 Which of these compounds, on complete combustion of one mole, will release the greatest amount of energy? A B C D CH3CH2CH2OH CH3CH2CH3 CH3CH2CO2H CH3COCH3 10 At high temperatures, steam decomposes into its elements according to the following equation. 2H2O(g) 2H2(g) + O2(g) In one experiment at 1 atm pressure, it was found that 20 % of the steam had been converted into hydrogen and oxygen. What are the values of the equilibrium partial pressures, in atm, of the components of this equilibrium? partial pressure of steam A B C D partial pressure of hydrogen partial pressure of oxygen 0.80 x 1 1.0 0.80 x 1 1.0 0.80 x 1 1.0 0.10 x 1 1.0 0.133 x 1 1.0 0.20 x 1 1.0 0.20 x 1 1.1 0.10 x 1 1.0 0.067 x 1 1.0 0.10 x 1 1.0 0.10 x 1 1.1 0.80 x 1 1.1  UCLES 2004 9701/01/O/N/04 www.xtremepapers.net 5 11 Which statement concerning the equilibrium reaction below is true? 2 2CrO 4 (aq) + 2H + (aq) _ 2 Cr2 O 7 (aq) + H 2 O(l) _ A B C D An increase in acid concentration will result in an increase in the concentration of 2_ Cr2 O 7 (aq). A redox reaction is taking place. 2 The addition of a catalyst will result in an increase in the concentration of Cr2 O 7 (aq) . _ The equilibrium constant, Kc, has no units.  UCLES 2004 9701/01/O/N/04 [Turn over www.xtremepapers.net 6 12 The diagram shows the Boltzmann distribution for air at room temperature. fraction of molecules 0 0 energy Air inside a car engine can reach a temperature of about 500 °C, enabling nitrogen to react with oxygen to form nitrogen oxides. What would be the Boltzmann distribution for the air inside this car engine? A B fraction of molecules fraction of molecules 0 0 energy C 0 0 energy D fraction of molecules fraction of molecules 0 0 energy 0 0 energy  UCLES 2004 9701/01/O/N/04 www.xtremepapers.net 7 13 burette conical flask Which of these acid-base (neutralisation) reactions could be titrated using the apparatus shown above to give a sharp end-point? A B C D sulphuric acid and aluminium oxide sulphuric acid and magnesium hydroxide sulphuric acid and magnesium oxide sulphuric acid and sodium hydroxide 14 The species Ar, K+ and Ca2+ are isoelectronic (have the same number of electrons). In what order do their radii increase? smallest A B C D Ar Ar Ca2+ K + largest Ca2+ K+ K+ Ar K+ Ca2+ Ar Ca 2+  UCLES 2004 9701/01/O/N/04 [Turn over www.xtremepapers.net 8 15 Strontium metal can be obtained by the electrolysis of molten strontium bromide, SrBr2, using the apparatus shown in the diagram. steel cathode graphite anode atmosphere of argon molten strontium molten strontium bromide heat Why is an atmosphere of argon used around the cathode? A B C D The argon keeps the strontium molten. The argon stops the molten strontium rising too high in the tube. A thin film of a compound of strontium and argon forms on the surface protecting the freshly formed metal. Without the argon strontium oxide would form in the air. 16 A weedkiller can be prepared by heating a bleach solution. 3NaCl O bleach heat 2NaCl + NaCl O3 weedkiller What are the oxidation states of chlorine in these three compounds? A B C D –1 +1 +1 +2 –1 –1 –1 +1 +5 +5 +7 +7  UCLES 2004 9701/01/O/N/04 www.xtremepapers.net 9 17 The following report appeared in a newspaper. Drums of bromine broke open after a vehicle crash on the motorway. Traffic was diverted as purple gaseous bromine drifted over the road (it is denser than air), causing irritation to drivers’ eyes. Firemen sprayed water over the scene of the accident, dissolving the bromine and washing it away. What is wrong with the report? A B C D Bromine does not dissolve in water. Bromine does not vapourise readily. Bromine is less dense than air. Bromine is not purple. 18 Which reaction of ammonia does not involve the non-bonding pair of electrons on the nitrogen atom? A B C D + NH3(g) + CH3I(g) → CH3NH 3 I –(s) NH3(g) + HCl (g) → NH4Cl (s) 2NH3(l) + 2Na(s) → 2NaNH2(s) + H2(g) 2NH3(aq) + Ag (aq) → [Ag(NH3)2] (aq) + + 19 Ammonium sulphate in nitrogenous fertilisers in the soil can be slowly oxidised by air producing sulphuric acid, nitric acid and water. How many moles of oxygen are needed to oxidise completely one mole of ammonium sulphate? A 1 B 2 C 3 D 4 20 What can behave as an electrophilic reagent? A B C D Br2 Na NH3 CN –  UCLES 2004 9701/01/O/N/04 [Turn over www.xtremepapers.net 10 21 Which molecule does not have a chiral centre? A CO2H H HO C C OH H H H B CO2H C C CH3 D OH OH OH OH OH CO2H C OH C HO CH3 C HO CO2C2H5 22 Instead of obtaining buta-1,3-diene from fossil fuel sources, it is proposed to obtain it from ethanol, which can be obtained from non–food agricultural crops. The sequence of reactions is as follows. step I CH3CH2OH CH3CHO step II CH3CH(OH)CH2CHO step III CH2=CHCH=CH2 buta-1,3-diene Which term could be used to describe step I? A B C D condensation dehydration dehydrogenation hydrogenation 23 How many different substitution products are possible, in principle, when a mixture of bromine and ethane is allowed to react? A 3 B 5 C 7 D 9  UCLES 2004 9701/01/O/N/04 www.xtremepapers.net 11 24 This molecule is responsible for the flavour of spearmint chewing gum. CH3 X H C O C C Y C H H C H H C H C H C H H What is a true statement about the functional groups X or Y? A B C D X will undergo nucleophilic addition. Y will undergo nucleophilic addition. X will undergo electrophilic substitution. Y will undergo electrophilic substitution. 25 Which reaction occurs with saturated hydrocarbons? A B C D catalytic hydrogenation ready decolourisation of aqueous bromine polymerisation thermal cracking 26 The reaction of chlorine with methane is carried out in the presence of light. What is the function of the light? A B C D to break the C – H bonds in methane to break up the chlorine molecules into atoms to break up the chlorine molecules into ions to heat up the mixture  UCLES 2004 9701/01/O/N/04 [Turn over www.xtremepapers.net 12 27 Use of the Data Booklet is relevant to this question. Which of the bonds in the structure below has the lowest bond energy? H A H C H B F C C H D Cl 28 Which isomer of C5H11OH gives, on dehydration, the greatest number of different alkenes? A CH3 CH2 CH CH3 B CH3 CH2 CH2 CH OH C CH3 CH2 CH OH D CH3 CH CH3 CH2 CH2OH CH2 CH3 CH3 CH2OH 29 The solvent methylisobutylketone, MIBK, can be made from propanone. H H H H C C C H H H C H H O C H C H H Which reagent could distinguish this compound from an aldehyde? A B C D Br2(aq) 2,4-dinitrophenylhydrazine NaBH4 Tollens’ reagent  UCLES 2004 9701/01/O/N/04 www.xtremepapers.net 13 30 Acarol is sold as an insecticide for use on fruit and vegetables. OH O Br C C O CH3 CH CH3 Br Acarol The final stage of its manufacture is an esterification. Which alcohol is used to form the ester? A B C D di(4-bromophenyl)methanol methanol propan-1-ol propan-2-ol  UCLES 2004 9701/01/O/N/04 [Turn over www.xtremepapers.net 14 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 The diagram illustrates the energy changes of a set of reactions. H = _134 kJ mol R _ 1 S H = +92 J mol 1 T H = _75 kJ mol _ 1 U Which of the following statements are correct? 1 2 3 The enthalpy change for the transformation U → R is + 42 kJ mol–1 . The enthalpy change for the transformation T → S is endothermic. The enthalpy change for the transformation R → T is – 33 kJ mol–1 .  UCLES 2004 9701/01/O/N/04 www.xtremepapers.net 15 32 Ammonia is produced commercially by the Haber process in which nitrogen and hydrogen react as shown. N2(g) + 3H2(g) 2NH3(g) ; ∆H = – 92 kJ mol–1 Which statements are true of the commercial process? 1 2 3 A temperature of 1000 oC is used. A pressure of 100 - 200 atm is used. The yield of ammonia is less than 20 %. 33 What factors can affect the value of the activation energy of a reaction? 1 2 3 the presence of a catalyst changes in temperature changes in concentration of the reactants 34 The first ionisation energies of successive elements in the Periodic Table are represented in the graph. 2500 2000 1500 first ionisation _ energy / kJ mol 1 1000 500 0 A B C D E F G H I J K L M N O P Q R S T element Which of these statements about this graph are correct? 1 2 3 Elements B, J and R are in Group 0 of the Periodic Table. Atoms of elements D and L contain 2 electrons in their outer shells. Atoms of elements G and O contain half-filled p orbitals.  UCLES 2004 9701/01/O/N/04 [Turn over www.xtremepapers.net 16 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 35 Which reactions involving calcium and its compounds would produce two gaseous products? 1 2 3 heating solid anhydrous calcium nitrate heating solid anhydrous calcium carbonate adding calcium metal to water 36 Which properties in the sequence hydrogen chloride, hydrogen bromide and hydrogen iodide steadily increase? 1 2 3 thermal stability bond length ease of oxidation 37 Which compounds may result from mixing ethane and chlorine in the presence of sunlight? 1 2 3 CH3CH2Cl CH3CH2CH2CH3 CH3CHCl CHCl CH3  UCLES 2004 9701/01/O/N/04 www.xtremepapers.net 17 38 When halogenoalkanes, RX, are hydrolysed with NaOH, the corresponding sodium halide, NaX, is produced. RX + NaOH → ROH + NaX A student investigated the amount of NaX produced by hydrolysing CH3CH2Cl and another halogenoalkane, Y. In a given time the amount of sodium halide formed was greater with Y than with CH3CH2Cl. number of moles of NaX formed Y CH3CH2Cl 0 0 time Which compound could be Y? 1 2 3 Cl CH2CH2Cl CH3CH2Br CH3CH2I 39 Pentaerythritol is an intermediate in the manufacture of paint. HOCH2 HOCH2 C CH2OH CH2OH pentaerythritol Which of the following statements about pentaerythritol are correct? 1 2 3 It reacts with metallic sodium. It is dehydrated by concentrated sulphuric acid to an alkene. Its empirical formula is CH3O.  UCLES 2004 9701/01/O/N/04 [Turn over www.xtremepapers.net 18 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 40 Lactic acid builds up in muscles when oxygen is in short supply. It can cause muscular pain. Part of the reaction sequence is shown. CH2OHCH(OH)CHO → CH3COCO2H → CH3CH(OH)CO2H glyceraldehyde pyruvic acid lactic acid Which statements about the reaction sequence are correct? 1 2 3 An aldehyde is oxidised to a carboxylic acid. A ketone is reduced to a secondary alcohol. A secondary alcohol is oxidised to a ketone.  UCLES 2004 9701/01/O/N/04 www.xtremepapers.net 19 BLANK PAGE 9701/01/O/N/04 www.xtremepapers.net 20 BLANK PAGE University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES) which is itself a department of the University of Cambridge. 9701/01/O/N/04 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice October/November 2005 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the answer sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C, and D. Choose the one you consider correct and record your choice in soft pencil on the separate answer sheet. Read the instructions on the answer sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. You may use a calculator. This document consists of 13 printed pages and 3 blank pages. IB05 11_9701_01/RP  UCLES 2005 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 The petrol additive tetraethyl-lead(IV), Pb(C2H5)4, is now banned in many countries. When it is completely burned in air, lead(II) oxide, CO2 and H2O are formed. How many moles of oxygen are required to burn one mole of Pb(C2H5)4? A 9.5 B 11 C 13.5 D 27 2 Which ion has more electrons than protons and more protons than neutrons? [H = 1 H ; D = 1 A D– B H3O+ C 2 1H ;O= 16 8 O] OD– D OH– 3 What is the electronic configuration of an element with a second ionisation energy higher than that of each of its neighbours in the Periodic Table? A B C D 1s22s22p63s2 1s22s22p63s23p1 1s22s22p63s23p2 1s22s22p63s23p3 4 Which compound has a boiling point that is influenced by hydrogen bonding? A B C D CH3CHO CH3OCH3 HCO2H HCO2CH3 5 Which gas is likely to deviate most from ideal gas behaviour? A HCl B He C CH4 D N2 6 Given and S(s) + O2(g) → SO2(g), 1 S(s) + 12 O2(g) → SO3(g) ∆H o = –297 kJ mol –1 f ∆H o = –395 kJ mol –1 f what is the enthalpy change of reaction, ∆H o, of 2SO2(g) + O2(g) → 2SO3(g)? A –196 kJ mol –1 B –98 kJ mol –1 C +98 kJ mol –1 D +196 kJ mol –1 © UCLES 2005 9701/01/O/N/05 www.xtremepapers.net 3 7 The table shows the enthalpy change of neutralisation per mole of water formed, ∆H, for various acids and bases. acid hydrochloric acid P hydrochloric acid nitric acid What are P, Q and R? P A B C D ethanoic acid ethanoic acid sulphuric acid sulphuric acid Q ammonia sodium hydroxide ammonia sodium hydroxide R potassium hydroxide ammonia potassium hydroxide ammonia base sodium hydroxide sodium hydroxide Q R ∆H / kJ mol–1 –57.0 –54.0 –52.0 –57.0 8 During the electrolysis of brine using a diaphragm cell, which reaction occurs at the cathode? A B C D 2Cl –(aq) → Cl2(g) + 2e– 4OH –(aq) → O2(g) + 2H2O(l) + 4e– 2H2O(l) + 2e– → H2(g) + 2OH–(aq) Na+(aq) + e– → Na(s) 9 Chlorine dioxide is produced on a large scale as it is used for bleaching paper pulp. It is made by the following reaction. 2Cl O3(aq) + SO2(g) → 2Cl O2(g) + SO 2 − (aq) 4 How do the oxidation numbers of chlorine and sulphur change in this reaction? chlorine A B C D decreases by 1 decreases by 1 decreases by 3 decreases by 3 sulphur increases by 1 increases by 2 increases by 1 increases by 2 − © UCLES 2005 9701/01/O/N/05 [Turn over www.xtremepapers.net 4 10 An experiment is set up to measure the rate of hydrolysis of methyl ethanoate. CH3CO2CH3 + H2O CH3CO2H + CH3OH The hydrolysis is found to be slow in neutral aqueous solution but it proceeds at a measurable rate when the solution is acidified with hydrochloric acid. What is the function of the hydrochloric acid? A B C D to dissolve the methyl ethanoate to ensure that the reaction reaches equilibrium to increase the reaction rate by catalytic action to suppress ionisation of the ethanoic acid formed 11 The distribution of molecular kinetic energies within a gas at temperature T1 and T2 are shown in the diagram. fraction of total molecules T1 T2 > T1 Ea = activation energy T2 Ea 0 0 kinetic energy Which statement correctly explains why a small increase in temperature leads to a significant increase in the rate of a gaseous reaction? A B C D The frequency of collisions between molecules is greater at a higher temperature. The activation energy of the reaction is less when the gases are at a higher temperature. The frequency of collisions between molecules with kinetic energy greater than the activation energy is greater at higher temperature. The proportion of molecules with more kinetic energy than the activation energy is lower at a higher temperature. © UCLES 2005 9701/01/O/N/05 www.xtremepapers.net 5 12 One mole of magnesium, aluminium and sulphur are each completely burned in an excess of oxygen gas. Which graph shows the moles of oxygen used in each case? A moles of oxygen used moles of oxygen used B 0 Mg Al C moles of oxygen used moles of oxygen used S 0 Mg Al D S 0 Mg Al S 0 Mg Al S 13 In 1999, researchers working in the USA believed that they had made a new element and that it had the following electronic structure. [Rn] 5f146d107s27p6 In which Group of the Periodic Table would you expect to find this element? A II B IV C VI D 0 14 Consecutive elements X, Y, Z are in Period 3 of the Periodic Table. Element Y has the highest first ionisation energy and the lowest melting point. What could be the identities of X, Y and Z ? A B C D sodium, magnesium, aluminium magnesium, aluminium, silicon aluminium, silicon, phosphorus silicon, phosphorus, sulphur © UCLES 2005 9701/01/O/N/05 [Turn over www.xtremepapers.net 6 15 Use of the Data Booklet is relevant to this question. What volume of oxygen, measured under room conditions, can be obtained from the thermal decomposition of 8.2 g of calcium nitrate (Mr = 164)? A 150 cm3 B 300 cm3 C 600 cm3 D 1200 cm3 16 When a mineral was heated in a Bunsen flame to constant mass, a colourless gas that turned lime water milky was evolved. The remaining solid was cooled and then added to aqueous hydrochloric acid. Vigorous effervescence was seen. What was the mineral? A B C D aragonite, CaCO3 artinite, MgCO3.Mg(OH)2.3H2O barytocalcite, BaCO3.CaCO3 dolomite, CaCO3.MgCO3 17 How does ammonia behave when its aqueous solution is used to dissolve silver chloride, AgCl ? A B C D as a base as a ligand with the Ag+ ion as a ligand with the Cl – ion as a reducing agent 18 Lime, CaO, is used to reduce the acidity of soil, and ammonium sulphate is a nitrogenous fertiliser. Why can they not be used in a mixed form? A B C D The dry mixture is explosive. CaSO4, formed on mixing, causes hard water. When dampened, ammonia is given off. Sulphuric acid will form. 19 The diagram shows the structure of vitamin C. HO C O C O OH C CH CH OH CH2OH How many chiral centres are there in one molecule? A 1 B 2 C 3 D 4 © UCLES 2005 9701/01/O/N/05 www.xtremepapers.net 7 20 What is the number of isomers of C2H2Cl2 including cis-trans isomers? A 2 B 3 C 4 D 5 21 Which hydrocarbon, on treatment with hot acidified potassium manganate(VII), would give ethanoic acid only? A B CH3CH CH3CH CH3 C CH3 CH3 C CH3 CH2 CHCH3 C CHCH3 CH3 C CH3 D 22 In the upper atmosphere chlorofluoroalkanes (CFCs) are broken down to give chlorine radicals but not fluorine radicals. What is the best explanation for this? A B C D Fluorine is more electronegative than chlorine. Fluorine radicals are less stable than chlorine radicals. The C–F bond is stronger than the C–Cl bond. The chlorine atom is larger than the fluorine atom. 23 An amine is produced in the following reaction. C2H5I + 2NH3 → C2H5NH2 + NH4I What is the mechanism? A B C D electrophilic addition electrophilic substitution nucleophilic addition nucleophilic substitution © UCLES 2005 9701/01/O/N/05 [Turn over www.xtremepapers.net 8 24 Compound X on reaction with hot concentrated sulphuric acid gave a mixture of three alkenes. What could X be? A B C D butan-2-ol propan-2-ol 2-methylbutan-2-ol 2-methylpropan-2-ol 25 Compounds X, Y and Z all react with PCl5 to release hydrogen chloride, but only one of them reacts with 2,4-dinitrophenylhydrazine reagent. Which one of the following combinations could be X, Y and Z ? X A CH2OH CH2OH B CH2OH CH2OH C CH2OH CHO CH2OH CO2H Y CHO CHO CH2OH CHO CH2OH CO2H CHO CO2H Z CO2H CO2H CHO CO2H CHO CO2H CO2H CO2H D 26 In 1903 Arthur Lapworth became the first chemist to investigate a reaction mechanism. The reaction he investigated was that of hydrogen cyanide with propanone. What do we now call the mechanism of this reaction? A B C D electrophilic addition electrophilic substitution nucleophilic addition nucleophilic substitution © UCLES 2005 9701/01/O/N/05 www.xtremepapers.net 9 27 What is formed when propanone is refluxed with an anhydrous solution of NaBH4? A B C D propanal propan-1-ol propan-2-ol propane 28 What is the structure of the ester formed from propanoic acid and ethanol? A H H C H C O O H C H C H H C H C H O H O H C C C H H H H H H C H C H C H H C H H H H C H H C H C B O H O C H D O H O C H H C H H H C H H 29 Lactic acid occurs naturally, for example in sour milk. Its displayed formula is shown. H H H C H O C H C O H O Which reaction occurs with lactic acid? A B C D It decolourises aqueous bromine rapidly. It is insoluble in water. It reduces Fehling’s reagent. Two molecules react with each other in the presence of a strong acid. © UCLES 2005 9701/01/O/N/05 [Turn over www.xtremepapers.net 10 30 PHB (polyhydroxybutyric acid) is a natural polymer produced by a range of micro-organisms. It can also be manufactured from sugar. PHB is readily biodegradable. CH3 O CH2 C [n [ O CH PHB (polyhydroxybutyric acid) What type of reaction will cause PHB to break down? A B C D addition hydrolysis reduction substitution © UCLES 2005 9701/01/O/N/05 www.xtremepapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 The relative molecular mass of a molecule of chlorine is 72. Which properties of the atoms in this molecule are the same? 1 2 3 radius nucleon number relative isotopic mass 32 Which molecules are planar? 1 2 3 BCl3 NH3 PH3 33 Boron is a non-metallic element which is placed above aluminium in Group III of the Periodic Table. It forms a compound with nitrogen known as boron nitride which has a graphite structure. Which of the following conclusions can be drawn from this information? 1 2 3 The empirical formula of boron nitride is BN. The boron and nitride atoms are likely to be arranged alternately in a hexagonal pattern. Boron nitride has a layer structure with van der Waals’ forces between the layers. © UCLES 2005 9701/01/O/N/05 [Turn over www.xtremepapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 34 Hydroxyapatite, Ca5(PO4)3OH, is the main constituent of tooth enamel. In the presence of saliva, the following equilibria exist. Ca5(PO4)3OH(s) 2 HPO4 −(aq) 3 5Ca2+(aq) + 3PO4 −(aq) + OH–(aq) 3− H+(aq) + PO4 (aq) Which of the following statements help to explain why tooth enamel is dissolved more readily when saliva is acidic? 1 2 3 The hydroxide ions are neutralised by the acid. 3 The phosphate ion PO4 −(aq) accepts H+(aq) Calcium ions react with acids. 35 What properties enable magnesium oxide to be used as a refractory lining in a furnace? 1 2 3 It has a high melting point. It has a low thermal conductivity. It does not react with basic slags. 36 Chlorine reacts with hot concentrated aqueous sodium hydroxide according to the equation below. 3Cl2(g) + 6NaOH(aq) → NaCl O3(aq) + 5NaCl (aq) + 3H2O(l) Which conclusions can be drawn from this information? 1 2 3 The oxidation state of the chlorine in one of the products is +5. The chlorine undergoes disproportionation. The sodium hydroxide acts as a reducing agent. © UCLES 2005 9701/01/O/N/05 www.xtremepapers.net 13 37 Which equations represent stages in the Contact process for manufacturing sulphuric acid? 1 2 3 S + O2 → SO2 H2O + SO2 → H2SO3 1 H2SO3 + 2 O2 → H2SO4 38 For the reaction (CH3)3SiCl + C2H5O– → (CH3)3SiOC2H5 + Cl – which statements are likely to be true? 1 2 3 It involves nucleophilic attack by C2H5O–. Cl – is displaced by C2H5O–. The oxygen-carbon bond is not broken. 39 Modern cars are fitted with catalytic converters. These remove carbon monoxide, unburnt hydrocarbons and oxides of nitrogen from exhaust gases. Which of these pollutant gases are removed by oxidation? 1 2 3 carbon monoxide hydrocarbons nitrogen oxides 40 The sex-attractant of the house-fly is muscalure, with the following formula. CH3(CH2)7CH = CH(CH2)12CH3 Which statements about muscalure are correct? 1 2 3 It will decolourise aqueous bromine. It will be oxidised by cold aqueous alkaline KMnO4 to give a diol. It will be optically active. © UCLES 2005 9701/01/O/N/05 www.xtremepapers.net 14 BLANK PAGE 9701/01/O/N/05 www.xtremepapers.net 15 BLANK PAGE 9701/01/O/N/05 www.xtremepapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. 9701/01/O/N/05 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice October/November 2006 1 hour Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 15 printed pages and 1 blank page. IB06 11_9701_01/3RP  UCLES 2006 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 The amount of calcium ions in a sample of natural water can be determined by using an ionexchange column as shown in the diagram. water sample ion-exchange resin A 50 cm3 sample of water containing dissolved calcium sulphate was passed through the ionexchange resin. Each calcium ion in the sample was exchanged for two hydrogen ions. The resulting acidic solution collected in the flask required 25 cm3 of 1.0 × 10–2 mol dm–3 potassium hydroxide for complete neutralisation. What was the concentration of the calcium sulphate in the original sample? A B C D 2.5 × 10–3 mol dm–3 1.0 × 10–2 mol dm–3 2.0 × 10–2 mol dm–3 4.0 × 10–2 mol dm–3 © UCLES 2006 9701/01/O/N/06 www.xtremepapers.net 3 2 Three successive elements in the Periodic Table have first ionisation energies which have the pattern shown in the diagram. x x first ionisation energy x atomic number What could be the first element of this sequence? A 3 C B N C F D Na Use of the Data Booklet is relevant to this question. The electronic structures of calcium, krypton, phosphorus and an element X are shown. Which electronic structure is that of element X? A B C D 1s22s22p63s23p3 1s22s22p63s23p64s2 1s22s22p63s23p63d64s2 1s22s22p63s23p63d104s24p6 © UCLES 2006 9701/01/O/N/06 [Turn over www.xtremepapers.net 4 4 Samples of 10 cm3 of each of the first four members of the alkane series are separately mixed with 70 cm3 of oxygen. Each is then burned and the total volume, V, of residual gas measured again at room temperature and pressure. Which graph represents the results that would be obtained? A V / cm3 80 60 40 X 20 X 0 CH4 C 2H 6 C3H 8 C4H10 0 CH4 X 20 X V / cm3 B X 80 X 60 X 40 X C 3H 8 C 2H 6 C4H10 C V / cm 3 D V / cm 3 80 60 X 40 20 0 CH4 C 2H 6 C3H 8 C4H10 X X X 80 60 40 20 0 CH4 C 2H 6 C 3H 8 C4H10 X X X X © UCLES 2006 9701/01/O/N/06 www.xtremepapers.net 5 5 Which diagram describes the formation of a π bond from the overlap of its orbitals? A B C D 6 For an ideal gas, the plot of pV against p is a straight line. For a real gas, such a plot shows a deviation from ideal behaviour. The plots of pV against p for three real gases are shown below. The gases represented are ammonia, hydrogen and nitrogen. X Y Z ideal gas pV 0 0 p What are the identities of the gases X, Y and Z? X A B C D ammonia hydrogen nitrogen nitrogen Y nitrogen nitrogen ammonia hydrogen Z hydrogen ammonia hydrogen ammonia © UCLES 2006 9701/01/O/N/06 [Turn over www.xtremepapers.net 6 7 Magnesium oxide may be used for the lining of an electric furnace for making crockery. Which properties of magnesium oxide help to explain this use? strong forces between particles A B C D 8 yes yes no no ionic bonding yes no yes no electrical conductor no yes no yes For which equation is the enthalpy change correctly described as an enthalpy change of formation? A B C D 2NO(g) → N2(g) + O2(g) 2CO(g) + O2(g) → 2CO2(g) H2O(l) + NaCl(s) → NaCl(aq) K(s) + Mn(s) + 2O2(g) → KMnO4(s) 1 2 1 2 9 Given CO(g) + H2(g) + H2O(g) O2(g) → → → CO2(g) H2O(l) H2O(l) ∆Ho = –283 kJ mol–1 ∆Ho = –286 kJ mol–1 ∆Ho = –44 kJ mol–1 O2(g) what is the change in enthalpy, ∆Ho, for the following reaction? CO2(g) + H2(g) → CO(g) + H2O(g) A –525 kJ mol–1 B –41 kJ mol–1 C +41 kJ mol–1 D +525 kJ mol–1 10 In some early paintings, lead(II) carbonate was used as a white pigment. In the 19th century hydrogen sulphide from burning coal reacted with this pigment to form black lead(II) sulphide, PbS. The original colour of the painting may be restored by carefully treating the area with dilute hydrogen peroxide, producing lead(II) sulphate which is also white. What is the role of the hydrogen peroxide? A B C D catalyst oxidising agent reducing agent solvent © UCLES 2006 9701/01/O/N/06 www.xtremepapers.net 7 11 The equilibrium constant, Kc, for the reaction to form ethyl ethanoate from ethanol and ethanoic CH3CO2C2H5 + H2O, at 60 oC is 4.00. acid, C2H5OH + CH3CO2H When 1.00 mol each of ethanol and ethanoic acid are allowed to reach equilibrium at 60 oC, what is the number of moles of ethyl ethanoate formed? A 1 3 B 2 3 C 1 4 D 3 4 12 The diagram shows the Maxwell-Boltzmann energy distribution curves for molecules of a sample of a gas at two different temperatures. Which letter on the axes represents the most probable energy of the molecules at the lower temperature? A B C D 13 Steam is passed over heated magnesium to give compound X and hydrogen. What is not a property of compound X? A B C D It has a high melting point. It is a basic oxide. It is a white solid. It is very soluble in water. 14 A 5.00 g sample of an anhydrous Group II metal nitrate loses 3.29 g in mass on strong heating. Which metal is present? A B C D magnesium calcium strontium barium 9701/01/O/N/06 © UCLES 2006 [Turn over www.xtremepapers.net 8 15 Which of the following is not a correct statement about iodine? A B C D A crystal of iodine contains covalent bonds and van der Waals’ forces. Iodine vapour is purple. The first ionisation energy of iodine is less than that of bromine. The hydride of iodine is of greater thermal stability than that of bromine. 16 Mixing aqueous silver nitrate and aqueous sodium chloride produces a precipitate. Addition of which reagent to the mixture gives a colourless solution? A B C D aqueous ammonia aqueous potassium iodide dilute hydrochloric acid dilute nitric acid 17 Which is the complete list of all the products from the reaction of concentrated sulphuric acid with potassium bromide? A B C D potassium hydrogensulphate and hydrogen bromide potassium hydrogensulphate, hydrogen bromide and bromine potassium hydrogensulphate, hydrogen bromide, bromine and water potassium hydrogensulphate, hydrogen bromide, bromine, water and sulphur dioxide 18 Sulphur dioxide is an important food preservative. Which property makes sulphur dioxide useful in this role? A B C D It is a gas. It is a reducing agent. It reacts with oxygen to form sulphur trioxide. It reacts with water to form an acidic solution. © UCLES 2006 9701/01/O/N/06 www.xtremepapers.net 9 19 In the Contact process for the production of sulphuric acid, sulphur dioxide is mixed with air and passed over a vanadium(V) oxide catalyst at about 450 oC and a pressure slightly above atmospheric pressure. 2SO2 + O2 2SO3 ; ∆H negative What affects the choice of conditions for this reaction? A B C D A lower temperature would not raise the concentration of SO3 at equilibrium. At a lower temperature of 300 oC the V2O5 catalyst would not be effective. At 450 oC nitrogen and oxygen from the air combine to form nitrogen oxides which are needed as additional catalysts. The heat generated by the reaction raises the temperature of the catalyst bed to 600 oC at which temperature the reaction begins to take place. 20 In which class of compound, in its general formula, is the ratio of hydrogen atoms to carbon atoms the highest? A B C D alcohols aldehydes carboxylic acids halogenoalkanes 21 What is the total number of different chloroethanes, formula C2H6-nCln, where n can be any integer from 1 to 4? A 4 B 6 C 7 D 8 22 Which reaction is an example of nucleophilic substitution? A B C D CH3CH2Br → CH2=CH2 + HBr CH2=CH2 + HBr → CH3CH2Br C3H7Br + H2O → C3H7OH + HBr C2H6 + Br2 → C2H5Br + HBr © UCLES 2006 9701/01/O/N/06 [Turn over www.xtremepapers.net 10 23 Which alkene could exist in cis and trans forms? A B C CH3CH2CH2CH CH3CH2CH CH3CH2C CH3 D CH3CH CCH3 CH3 CH2 CHCH3 CH2 24 When gaseous chemicals are transported by road or by rail they are classified as follows. flammable Which gas is non-flammable? A B C D butane hydrogen oxygen propene non-flammable poisonous 25 Which equation or statement describes what happens when poly(propene) is burned in an excess of air? A B C D 1 (C3H6)n + 1 2 nO2 → 3nC + 3nH2O 1 (C3H6)n + 4 2 nO2 → 3nCO2 + 3nH2O (C3H6)n + 6nO2 → 3nCO2 + 3nH2O Poly(propene) does not burn. 26 When (chloromethyl)benzene, C6H5CH2Cl, is treated in succession with two reagents X and Y, it gives phenylethanoic acid, C6H5CH2CO2H. What are reagents X and Y? X A B C D NaOH(aq) Cl2(aq) NaCN (in aqueous ethanol) NaOH(aq) Y K2Cr2O7(aq) NaOH(aq) dilute H2SO4 CO2 © UCLES 2006 9701/01/O/N/06 www.xtremepapers.net 11 27 Which compound • • A B C D (CH3)2CHCOCH3 (CH3)3COH CH3CH2CH(OH)CH3 CH3CO2CH(CH3)2 is unaffected by hot alkaline potassium manganate(VII); gives hydrogen when treated with sodium? 28 A common industrial solvent is a mixture of propanone, CH3COCH3, and pentyl ethanoate CH3CO2(CH2)4CH3. Which reagent would have no effect on this solvent? A B C D Na(s) NaBH4 NaOH(aq) 2,4-dinitrophenylhydrazine reagent 29 Apples, the fruit of trees of the genus Malus, are rich in malic acid. Malic acid may be synthesised in the laboratory in two steps. step 1 NCCH2CHO X step 2 HO2CCH2CH(OH)CO2H malic acid Which reagents could be used for this synthesis? step 1 A B C D HCl (aq) HCN, NaCN(aq/alcoholic) H2SO4(aq) KCN(aq/alcoholic) step 2 HCN(g) H2SO4(aq) K2Cr2O7 / H2SO4(aq) HCl (aq) © UCLES 2006 9701/01/O/N/06 [Turn over www.xtremepapers.net 12 30 Which pair of compounds is formed when the ester C2H5CO2CH3 is boiled with aqueous sodium hydroxide? A B C D C2H5CO2H C2H5CO2Na C2H5CO2Na C2H5OH CH3OH CH3ONa CH3OH CH3CO2Na © UCLES 2006 9701/01/O/N/06 www.xtremepapers.net 13 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 The chlorine oxide free radical, ClO•, is formed during the depletion of the ozone layer by chlorofluoroalkanes (CFCs). Cl • + O3 → ClO• + O2 Which features are present in the chlorine oxide free radical? 1 2 3 an odd number of electrons a single covalent bond a dative covalent bond from oxygen to chlorine 32 Concentrated sulphuric acid behaves as a strong acid when it reacts with water. H2SO4(l) + aq → H+(aq) + HSO − (aq) 4 The HSO − ion formed behaves as a weak acid. 4 HSO − (aq) 4 H+(aq) + SO 2− (aq) 4 Which statements are true for 1.0 mol dm–3 sulphuric acid? 1 2 3 [H+(aq)] is high [ SO 2− (aq)] is high 4 [ HSO − (aq)] = [ SO 2− (aq)] 4 4 © UCLES 2006 9701/01/O/N/06 [Turn over www.xtremepapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 33 A reversible reaction is catalysed. Which statements about the effects of the catalyst on this system are correct? 1 2 3 The catalyst alters the mechanism of the reaction. The catalyst reduces the energy of activation (the energy barrier) for both the forward and the backward reaction. The catalyst alters the composition of the equilibrium mixture. 34 Which magnesium compounds lose mass when heated by a Bunsen flame? 1 2 3 magnesium carbonate magnesium nitrate magnesium oxide 35 What happens when chlorine is bubbled through aqueous sodium hydroxide solution? 1 2 3 In cold solution, ClO–(aq) ions are formed. In hot solution, ClO3–(aq) ions are formed. Disproportionation of chlorine occurs in both cold and hot aqueous solutions. 36 Which fertilisers, when washed out of soil by rain, cause excessive growth of river plants and algae with the result that fish in the river die? 1 2 3 K2SO4 NH4NO3 NaNO3 © UCLES 2006 9701/01/O/N/06 www.xtremepapers.net 15 37 The following three hydrocarbons all occur naturally. Which of these will be split into two organic compounds, both containing a ketone group, when treated with hot acidified potassium manganate(VII)? 1 2 3 38 Which are properties of fluoroalkanes? 1 2 3 They are less reactive than the corresponding chloroalkanes. They are non-flammable. The C-F bond is stronger than a C-Cl bond. 39 Which compounds are able to react with concentrated sulphuric acid to give a product that will decolourise acidic potassium manganate(VII)? 1 2 3 (CH3)3COH CH3CH2CH(OH)CH3 CH3CO2H 40 Rofecoxib, an efficient drug against arthritis, has the following structure. R is an inert group. R CH2 C O * C C O Which reactions are possible with this structure? 1 2 3 The bond marked is hydrolysed by heating with aqueous sodium hydroxide. Aqueous bromine is decolourised. An orange precipitate is formed with 2,4-dinitrophenylhydrazine reagent. © UCLES 2006 9701/01/O/N/06 www.xtremepapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. 9701/01/O/N/06 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 October/November 2007 1 hour *6168355464* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 14 printed pages and 2 blank pages. IB07 11_9701_01/2RP © UCLES 2007 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Use of the Data Booklet is relevant to this question. When a sports medal with a total surface area of 150 cm2 was evenly coated with silver, using electrolysis, its mass increased by 0.216 g. How many atoms of silver were deposited per cm2 on the surface of the medal? A B C D 2 8.0 × 1018 1.8 × 1019 1.2 × 1021 4.1 × 1022 Use of the Data Booklet is relevant to this question. In forming ionic compounds, elements generally form an ion with the electronic structure of a noble gas. Which ion does not have a noble gas electronic structure? A I– B Rb+ C Sn2+ D Sr2+ 3 The first stage in the manufacture of nitric acid is the oxidation of ammonia by oxygen. wNH3(g) + xO2(g) → yNO(g) + zH2O(g) Which values for w, x, y and z are needed to balance the equation? w A B C D 4 4 5 6 x 5 6 6 5 y 4 4 5 6 z 6 5 4 4 © UCLES 2007 9701/01/O/N/07 www.xtremepapers.net 3 4 The graph shows the first thirteen ionisation energies for element X. ionisation energy number of electrons removed What can be deduced about element X from the graph? A B C D 5 It is in the second period (Li to Ne) of the Periodic Table. It is a d-block element. It is in Group II of the Periodic Table. It is in Group III of the Periodic Table. Hydrogen bonding can occur between molecules of methanal, HCHO, and molecules of liquid Y. What could liquid Y be? A B C D CH3OH CH3CHO CH3COCH3 CH3CO2CH3 6 Lycra is a polyurethane fibre used in the fashion industry. It is a polymer made from two monomers, one of which has the following formula. O=C=N–(CH2)n –N=C=O What is the O–C–N bond angle in this molecule? A 90 ° B 109 ° C 120 ° D 180 ° © UCLES 2007 9701/01/O/N/07 [Turn over www.xtremepapers.net 4 7 What are the lattice structures of solid diamond, iodine and silicon(IV) oxide? giant molecular A B C D 8 diamond, silicon(IV) oxide diamond, iodine iodine silicon(IV) oxide simple molecular iodine silicon(IV) oxide diamond, silicon(IV) oxide diamond, iodine Which equation represents the standard enthalpy change of atomisation of bromine? A B C D Br2(l) → 2Br(g) Br2(g) → 2Br(g) 1 2 1 2 Br2(l) → Br(g) Br2(g) → Br(g) 9 In an experiment, 50.0 cm3 of a 0.10 mol dm–3 solution of a metallic salt reacted exactly with 25.0 cm3 of 0.10 mol dm–3 aqueous sodium sulphite. The half-equation for oxidation of sulphite ion is shown below. 2 SO 3− (aq) + H2O(I) → SO 2− (aq) + 2H+(aq) + 2e– 4 If the original oxidation number of the metal in the salt was +3, what would be the new oxidation number of the metal? A +1 B +2 C +4 D +5 10 Nitrogen dioxide decomposes on heating according to the following equation. 2NO2(g) 2NO(g) + O2(g) When 4 mol of nitrogen dioxide were put into a 1 dm3 container and heated to a constant temperature, the equilibrium mixture contained 0.8 mol of oxygen. What is the value of the equilibrium constant, Kc, at the temperature of the experiment? A 0 .8 2 × 0 .8 42 B 1 .6 × 0 .8 2.42 C 1 .6 2 × 0 . 8 42 D 1 .6 2 × 0 . 8 2 .4 2 © UCLES 2007 9701/01/O/N/07 www.xtremepapers.net 5 11 It is often said that the rate of a typical reaction is roughly doubled by raising the temperature by 10 °C. What explains this observation? A B C D Raising the temperature by 10 °C doubles the average kinetic energy of each molecule. Raising the temperature by 10 °C doubles the average velocity of the molecules. Raising the temperature by 10 °C doubles the number of molecular collisions in a given time. Raising the temperature by 10 °C doubles the number of molecules having more than a certain minimum energy. 12 When dangerous chemicals are transported by road, vehicles must carry signs that indicate what measures should be taken in the event of a spillage of the chemical carried. Which material must be used if there were a spillage of metallic sodium? A B C D ethanol jets of water sand water spray 13 Which species has the largest radius? A P3 − B Cl − C Ar D K+ 14 Use of the Data Booklet is relevant to this question. The sketch graph shows the variation of one physical or chemical property with another for the Group II elements. y x What are the correct labels for the axes? x-axis A B C D © UCLES 2007 y-axis mass number melting point atomic number atomic radius 9701/01/O/N/07 atomic number atomic number first ionisation energy first ionisation energy [Turn over www.xtremepapers.net 6 15 The chemical properties of an element at the top of a group in the Periodic Table are often different from those of the rest of the elements in the group. Of the following properties of beryllium and its compounds, which property is typical of the elements below it in Group II? A B C D Be does not react with hot water. BeCl2 is covalent. Be(NO3)2 produces BeO on thermal decomposition. BeO dissolves in alkalis. 16 Compound X on refluxing with aqueous sodium hydroxide gave mixture Y which on distillation with acidified potassium dichromate(VI) produced propanone. Mixing Y with dilute nitric acid and aqueous silver nitrate gave a cream precipitate. What could compound X be? A B C D CH3CHBrCH3 CH3CHICH3 CH3CH2CH2Br CH3CH2CH2I 17 There are three stages in the Contact process for the production of sulphuric acid. 1 2 3 S + O2 → SO2 SO2 + 1 2 O2 → SO3 SO3 + H2O → H2SO4 Which statement about this process is correct? A B C D In the first stage a large excess of air under high pressure is used to improve the yield. Two of the three stages are equilibria. All three stages are exothermic. In the final stage SO3 is absorbed by water droplets. 18 Gaseous nitrogen is less reactive than gaseous fluorine. What is the reason for this difference in reactivity? A B C D The boiling point of nitrogen is lower than that of fluorine. The relative molecular mass of nitrogen is lower than that of fluorine. The atomic radius of nitrogen is greater than that of fluorine. The bond strength in the molecule is greater in nitrogen than in fluorine. 9701/01/O/N/07 © UCLES 2007 www.xtremepapers.net 7 19 Which molecules, each with a linear carbon chain, can have an optically active isomer? I C3H6BrI A B C D I and II only I, II and III only II and III only I, II and IV only II C3H4BrI III C3H6I2 IV C3H4Br2 20 In which pair do the isomers have identical boiling points? A CH3CH2CH2CH2OH and (CH3)2CHCH2OH B CH3(CH2)4CH3 CH3 and (CH3)2CHCH(CH3)2 CH3 C H Cl CH3 C CH2Cl H C H C CH3 and Cl H 2 C CH3 and H C C H Cl CH3 C H D 21 Tetramethyl-lead(IV), (CH3)4Pb, increases the rate of the reaction of methane with chlorine. CH4(g) + Cl2(g) → CH3Cl(g) + HCl(g) Why can tetramethyl-lead(IV) behave in this way? A B C D It is a source of methyl radicals. + It releases CH3 (g) . It reacts with chloromethane and prevents equilibrium being established. Metal ions catalyse the reaction. © UCLES 2007 9701/01/O/N/07 [Turn over www.xtremepapers.net 8 22 Which reaction occurs when ethane and chlorine are mixed in diffused sunlight? A B C D a free-radical substitution with hydrogen given off a free-radical substitution with hydrogen chloride given off a free-radical substitution with no gas given off a nucleophilic substitution with hydrogen chloride given off 23 Limonene is an oil formed in the peel of citrus fruits. CH3 C CH2 CH3 limonene Which product is formed when molecular bromine reacts with limonene at room temperature in the dark? A CH3 C CH2 Br B CH3 C CH2 CH3 C Br C CH2Br CH3 D Br C CH2Br Br CH3 CH3 Br CH3 CH3 Br Br 24 The anaesthetic halothane, CF3CHBrCl, is made industrially as shown below. HF CCl2=CHCl stage 1 CF3CH2Cl Br2 stage 2 CF3CHBrCl Which type of reaction is occurring in stage 2? A B C D electrophilic addition electrophilic substitution free radical substitution nucleophilic addition © UCLES 2007 9701/01/O/N/07 www.xtremepapers.net 9 25 Chlorofluoroalkanes, CFCs, can be used as refrigerants, aerosol propellants and fire extinguishers. CFCs such as CCl3F and CCl2F2 are more stable than chloroalkanes such as CCl4. What is the reason for their greater stability? A B C D Fluorine has a higher first ionisation energy than chlorine. Fluorine radicals are more stable than chlorine radicals. The C–F bond energy is larger than the C–Cl bond energy. The C–F bond is more polar than the C–Cl bond. 26 Butanedioic acid occurs in amber, algae, lichens, sugar cane and beets. It may be synthesised in two steps from 1,2-dibromoethane. step 1 BrCH2CH2Br X step 2 HO2CCH2CH2CO2H Which reagents could be used for this synthesis? step 1 A B C D HCN(g) HCO2Na(aq) KCN(aq/alcoholic) NaOH(aq) step 2 HCl (aq) HCl (aq) H2SO4(aq) K2Cr2O7 / H2SO4(aq) 27 Which reaction will distinguish between a primary and a secondary alcohol? A B C D warming with H+ / MnO − 4 2 warming with H+ / Cr2O 7 − dehydration, followed by reaction with Br2(aq) oxidation, followed by reaction with Fehling’s (or Tollens’) reagent © UCLES 2007 9701/01/O/N/07 [Turn over www.xtremepapers.net 10 28 Hept-4-enal is present in cow’s milk. CH3CH2CH=CHCH2CH2CHO hept-4-enal What is formed when hept-4-enal is reduced with either hydrogen and a nickel catalyst or sodium borohydride? A B C D with H2 / Ni with H2 / Ni with NaBH4 with NaBH4 CH3(CH2)5CH2OH CH3(CH2)5CH3 CH3(CH2)5CH2OH CH3(CH2)5CHO 29 Which of these reactions is shown by butanone, CH3COCH2CH3? A B C D On warming with acidified potassium dichromate(VI) the solution turns green. On heating with Fehling’s reagent a red precipitate is formed. With 2,4-dinitrophenylhydrazine reagent an orange precipitate is formed. With hydrogen cyanide an aldehyde is formed. 30 The ester CH3CH2CH2CO2CH3 is responsible for the aroma of apples. When this ester is hydrolysed by acid in the stomach, what is the empirical formula of the organic acid produced? A CH4O B C2H4O C C2H4O2 D C3H7O2 © UCLES 2007 9701/01/O/N/07 www.xtremepapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 What are assumptions of the kinetic theory of gases and hence of the ideal gas equation, PV = nRT ? 1 2 3 Molecules move without interacting with one another except for collisions. Intermolecular forces are negligible. Intermolecular distances are much greater than the molecular size. 32 Carbon monoxide burns readily in oxygen to form carbon dioxide. What can be deduced from this information? 1 2 3 The +4 oxidation state of carbon is more stable than the +2 state. The standard enthalpy change of formation of carbon dioxide is more negative than that of carbon monoxide. The value of the equilibrium constant for the reaction, 2CO(g) + O2(g) be high. 2CO2(g), is likely to © UCLES 2007 9701/01/O/N/07 [Turn over www.xtremepapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 33 Phosphorus pentachloride is introduced into an empty gas syringe which has a movable, tightlyfitting plunger. The gas is allowed to expand until equilibrium is reached at a temperature at which the phosphorus pentachloride partially dissociates. PCl5(g) PCl3(g) + Cl2(g) self-sealing cap for introducing sample gas plunger syringe oven Which statements are correct? 1 2 3 The equilibrium pressure inside the syringe will be greater than atmospheric pressure. When the plunger is pushed in the equilibrium adjusts to produce more PCl5(g). The volume of gas in the syringe at equilibrium will be greater than if no dissociation had occurred. 34 Which statements are correct about the activation energy of a reaction? 1 It is different for the forward and back reactions in an exothermic process. 2 It is low for a reaction that takes place slowly. 3 It is unaffected by the presence of a catalyst. © UCLES 2007 9701/01/O/N/07 www.xtremepapers.net 13 35 When a firework is lit a fuel and an oxidising agent react. In such a firework, magnesium is the fuel and barium nitrate is the oxidising agent. Which solid products are produced when the firework is lit? 1 2 3 BaO MgO Mg(NO3)2 36 Why is the addition of concentrated sulphuric acid to solid potassium iodide unsuitable for the preparation of hydrogen iodide? 1 2 3 Hydrogen iodide is not displaced by sulphuric acid. Iodide ions are oxidised to iodine. The product is contaminated by sulphur compounds. 37 Which mixtures, on heating, produce the gas ND3? [D = 2 H , an isotope of hydrogen] 1 1 2 3 CaO(s) and ND4Cl(s) CH3CN and NaOD in D2O NDH3Cl and NaOD in D2O 38 Which structures show a primary alcohol that cannot be dehydrated to form an alkene? 1 2 3 CH3OH CH3CH2OH CH3CH(OH)CH3 39 In the reaction between an aldehyde and HCN catalysed by NaCN, which statements about the reaction mechanism are true? 1 2 3 A new carbon-carbon bond is formed. In the intermediate, the oxygen carries a negative charge. The last stage involves the formation of a hydrogen-oxygen bond. © UCLES 2007 9701/01/O/N/07 [Turn over www.xtremepapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 40 Monopotassium citrate is used as an emulsifying agent in powdered milk and in powdered soups. It may be represented by the formula shown. CH2CO2H HO C – CO2 K+ CH2CO2H Which statements about monopotassium citrate are correct? 1 2 3 It can form optical isomers. It can act as a dibasic acid. It can form esters with both acids and alcohols. © UCLES 2007 9701/01/O/N/07 www.xtremepapers.net 15 BLANK PAGE 9701/01/O/N/07 www.xtremepapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. 9701/01/O/N/07 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/01 October/November 2008 1 hour *8801464624* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 13 printed pages and 3 blank pages. IB08 11_9701_01/3RP © UCLES 2008 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Use of the Data Booklet is relevant to this question. Titanium(IV) oxide, TiO2, is brilliantly white and much of the oxide produced is used in the manufacture of paint. What is the maximum amount of TiO2 obtainable from 19.0 tonnes of the ore ilmenite, FeTiO3? A 2 10.0 tonnes B 12.7 tonnes C 14.0 tonnes D 17.7 tonnes Carbon disulphide vapour burns in oxygen according to the following equation. CS2(g) + 3O2(g) → CO2(g) + 2SO2(g) A sample of 10 cm3 of carbon disulphide was burned in 50 cm3 of oxygen. After measuring the volume of gas remaining, the product was treated with an excess of aqueous sodium hydroxide and the volume of gas measured again. All measurements were made at the same temperature and pressure, under such conditions that carbon disulphide was gaseous. What were the measured volumes? volume of gas after burning / cm3 A B C D 30 30 50 50 volume of gas after adding NaOH(aq) / cm3 0 20 20 40 3 In which pair do both atoms have one electron only in an s orbital in their ground states? A Ca, Sc B Cu, Be C H, He D Li, Cr 4 Use of the Data Booklet is relevant to this question. Hard water contains calcium ions and hydrogencarbonate ions arising from dissolved calcium hydrogencarbonate, Ca(HCO3)2. How many electrons are present in the hydrogencarbonate anion? A 30 B 31 C 32 D 33 © UCLES 2008 9701/01/O/N/08 www.xtremepapers.net 3 5 Which quantity would best indicate the relative strengths of the hydrogen bonds between the molecules in liquid hydrogen halides? A B C D 6 bond dissociation energies enthalpy changes of solution enthalpy changes of formation enthalpy changes of vaporisation A substance commonly found in the house or garden has the following properties. • It is combustible. • It is an electrical insulator. • It melts over a range of temperature. What could the substance be? A B C D brass paper poly(ethene) silicon(IV) oxide 7 Which of the following would behave most like an ideal gas at room temperature? A B C D carbon dioxide helium hydrogen nitrogen 8 Red lead oxide, Pb3O4, is used in metal priming paints. It can be made by heating PbO in air. 6PbO(s) + O2(g) → 2Pb3O4(s) Which two values are needed to calculate the enthalpy change for this reaction? A B C D enthalpy change of combustion of lead and enthalpy change of formation of Pb3O4 enthalpy change of combustion of PbO and enthalpy change of formation of Pb3O4 enthalpy change of formation of PbO and enthalpy change of atomisation of O2 enthalpy change of formation of PbO and enthalpy change of formation of Pb3O4 © UCLES 2008 9701/01/O/N/08 [Turn over www.xtremepapers.net 4 9 The diagram represents the reaction pathway for the following reaction. W(g) + X(g) → Y(g) + Z(g) energy W+X Y+Z reaction pathway What statement can be made about the reverse reaction, Y(g) + Z(g) → W(g) + X(g)? A B C D It will have a larger activation energy and a positive ∆H. It will have a larger activation energy and a negative ∆H. It will have a smaller activation energy and a positive ∆H. It will have a smaller activation energy and a negative ∆H. 2SO3(g), what will change the value of Kp? 10 For the equilibrium 2SO2(g) + O2(g) A B C D adding a catalyst adding more O2 increasing the pressure increasing the temperature 11 Dinitrogen tetroxide dissociates into nitrogen dioxide on heating. N2O4(g) 2NO2(g) In an experiment the partial pressures of the gases at equilibrium were found to be NO2, 0.33 atm; N2O4, 0.67 atm. What is the numerical value of Kp at the temperature of the experiment? A 0.16 B 0.49 C 0.65 D 2.03 © UCLES 2008 9701/01/O/N/08 www.xtremepapers.net 5 12 Crotonaldehyde, CH3CH=CHCHO, can be obtained by oxidising butadiene, CH2=CHCH=CH2, using air or oxygen. One method is to pass a mixture of butadiene and oxygen through a hot aqueous solution of palladium(II) ions, Pd2+(aq), which catalyse the reaction. Which statement is not correct about the action of the Pd2+(aq) ions? A B C D Changing the concentration of the Pd2+(aq) will have an effect on the rate of the reaction. Pd2+(aq) increases the energy of the reacting molecules. Pd2+(aq) lowers the activation energy for the reaction. When Pd2+(aq) is used, the reaction proceeds by a different route. 13 Which oxide, when mixed with water, will produce the most acidic solution? A CO B CO2 C SiO2 D P2O5 14 Which salt is produced by adding aqueous ammonia to aqueous sulphur dioxide until just alkaline? A NH4SO3 B NH4SO4 C (NH4)2SO3 D (NH4)2SO4 15 Aluminium chloride catalyses certain reactions by forming carbocations (carbonium ions) with chloroalkanes as shown. RCl + Al Cl3 → R+ + AlCl 4 Which property makes this reaction possible? A B C D AlCl3 exists as the dimer Al2Cl6 in the vapour. AlCl3 is a covalent molecule. The aluminium atom in Al Cl3 has an incomplete octet of electrons. The chlorine atom in RCl has a vacant p orbital. − 16 Due to their similar ionic radii, the reactions of lithium and magnesium and their corresponding compounds are very similar. Which statement concerning the reactions of lithium and its compounds is correct? A B C D Lithium carbonate decomposes on heating at a relatively low temperature, forming lithium oxide and carbon dioxide. Lithium nitrate decomposes on heating, forming lithium nitrite and oxygen. Lithium burns only slowly in oxygen. Lithium reacts violently with cold water, liberating hydrogen. © UCLES 2008 9701/01/O/N/08 [Turn over www.xtremepapers.net 6 17 A student observed the reactions when sodium chloride and sodium iodide were each reacted separately with concentrated sulphuric acid and concentrated phosphoric acid. The observations are recorded in the table. sodium chloride conc. H2SO4 conc. H3PO4 colourless acidic gas formed colourless acidic gas formed sodium iodide purple vapour formed colourless acidic gas formed Which deduction can be made from these observations? A B C D Concentrated phosphoric acid is a stronger oxidising agent than concentrated sulphuric acid. Concentrated phosphoric acid is a stronger oxidising agent than iodine. Concentrated sulphuric acid is a stronger oxidising agent than chlorine. Concentrated sulphuric acid is a stronger oxidising agent than iodine. 18 When gaseous chemicals are transported by road or by rail they are classified as follows. flammable Which gas is poisonous? A B C D butane carbon dioxide hydrogen sulphur dioxide non-flammable poisonous 19 Which statement explains the observation that magnesium hydroxide dissolves in aqueous ammonium chloride, but not in aqueous sodium chloride? A B C D The ionic radius of the NH4 ion is similar to that of Mg2+ but not that of Na+. NH4Cl dissociates less fully than NaCl. The Na+ and Mg2+ ions are isoelectronic (have the same number of electrons). The NH4 ion acts as an acid. + + © UCLES 2008 9701/01/O/N/08 www.xtremepapers.net 7 20 Sorbitol is a naturally-occurring compound with a sweet taste. It is often used as a substitute for sucrose by the food industry. The diagram shows its structure. H H H H O H H H C C C C C C H O O H O O O H H H H H How many chiral centres are present in sorbitol? A 1 B 2 C 3 D 4 21 The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass. CH3CH2CH=CHCH2CH2OH leaf alcohol Which two compounds will be formed when ‘leaf alcohol’ is oxidised using hot, concentrated manganate(VII) ions? A B C D CH3CO2H and HOCH2CH2CH2CO2H CH3CO2H and HO2CCH2CH2CO2H CH3CH2CO2H and HO2CCH2CO2H CH3CH2CO2H and HOCH2CH2CO2H 22 Which hydrocarbon can form a monochloro-substitution derivative which shows both chirality and cis-trans isomerism? A B C D CH3CH=CH2 (CH3)2C=CH2 CH3CH=C(CH3)2 CH3CH=CHCH2CH3 © UCLES 2008 9701/01/O/N/08 [Turn over www.xtremepapers.net 8 23 Four drops of 1-chlorobutane, 1-bromobutane and 1-iodobutane were put separately into three test-tubes containing 1.0 cm3 of aqueous silver nitrate at 60 °C. A hydrolysis reaction occurred. (R represents the butane chain C4H9– and X the halogen atom.) H2O(l) + R–X(l) + Ag+(aq) → R–OH(aq) + AgX(s) + H+(aq) The rate of formation of cloudiness in the tubes was in the order RCl < RBr < RI. Why is this? A B C D The R–X bond polarity decreases from RCl to RI. The solubility of AgX(s) decreases from AgCl to AgI. The ionisation energy of the halogen decreases from Cl to I. The bond energy of R–X decreases from RCl to RI. 24 A possible mechanism of the exothermic hydrolysis of 2-chloro-2-methylpropane is shown. CH3 CH3 C CH3 Cl slow CH3 CH3 C+ + Cl CH3 _ CH3 CH3 C+ + CH3 OH _ CH3 fast CH3 C CH3 OH Which diagram represents the reaction profile for this mechanism? A B C D energy energy energy energy reaction pathway reaction pathway reaction pathway reaction pathway © UCLES 2008 9701/01/O/N/08 www.xtremepapers.net 9 25 The functional group in a primary alcohol is –CH2OH. Which reagent reacts with a primary alcohol, under suitable conditions, to give an organic product with the same number of oxygen atoms as the alcohol? A Al2O3 B CH3CO2H C HBr D Na 26 Ethyl phenylethanoate, C6H5CH2CO2C2H5, gives a characteristic flowery aroma to honey. Which sequence of reagents, with heating in each case, leads to the preparation of C6H5CH2CO2C2H5 from C6H5CH2Br? A C6H5CH2Br NaOH(aq) C2H5COCl B C6H5CH2Br NaOH(aq) C2H5CO2H, conc. H2SO4 H+(aq) C C6H5CH2Br NaCN(alcoholic) C2H5OH, conc. H2SO4 D C6H5CH2Br NaOH(aq) – conc. MnO4, H+(aq) C2H5OH, conc. H2SO4 27 The stomach wall can become sensitive to acidic compounds. Which is the most acidic compound? A CO2H OCOCH3 B CO2H CH(OH) CH(OH) aspirin CH(OH) CH(OH) CH2OH gluconic acid C CO2H CH(OH) CH2 CO2H malic acid D CH3CH(OH)CO2H lactic acid © UCLES 2008 9701/01/O/N/08 [Turn over www.xtremepapers.net 10 28 Bees use 2-methylbutyl ethanoate as an ‘alarm’ pheromone. When disturbed, individual bees on guard will raise their abdomen and emit the alarm pheromone, fanning their wings to aid its dispersal. This alerts other bees to a danger and makes them ready to sting when required. H H C H C O O H C H C H C H C H H H H H C H H 2-methylbutyl ethanoate Which starting materials would be required to synthesise 2-methylbutyl ethanoate? A B C D CH3CH2OH and CH3CH2CH(CH3)CO2H CH3CO2H and CH3CH2CH(CH3)CH2OH CH3CH2OH and CH3CH2CH(CH3)CH2CO2H CH3CO2H and CH3CH2CH(CH3)CH2CO2H 29 The product of the reaction between propanone and hydrogen cyanide is hydrolysed under acidic conditions. What is the formula of the final product? A B C D CH3CH(OH)CO2H CH3CH2CH2CO2H (CH3)2CHCONH2 (CH3)2C(OH)CO2H 30 Use of the Data Booklet is relevant to this question. Ethyl ethanoate can be obtained from ethanoic acid and ethanol by the following reaction. CH3CH2OH + CH3CO2H CH3CO2CH2CH3 + H2O Ethanol (30 g) and ethanoic acid (30 g) are heated under reflux together, and 22 g of ethyl ethanoate are obtained. What is the yield of the ester? A 25 % B 38 % C 50 % D 77 % © UCLES 2008 9701/01/O/N/08 www.xtremepapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Kevlar has the structure below. O C O C N H N H O C O C N H N H Compared to a steel rope of similar dimensions, a Kevlar rope is both lighter and stronger. Which properties of Kevlar help to explain these facts? 1 2 3 The fibres of Kevlar align due to hydrogen bonding. The mass per unit length is less in a Kevlar rope than in a steel rope. The Kevlar molecule has no permanent dipole. 32 Which of the following can act as a Bronsted-Lowry acid? 1 2 3 H3O+ NH 4 H2O + 33 Under given conditions, what governs the rate of a forward reaction? 1 2 3 the activation energy of the reaction the enthalpy change of the reaction the equilibrium constant of the reaction © UCLES 2008 9701/01/O/N/08 [Turn over www.xtremepapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 34 Which statements concerning the Group II elements magnesium, calcium and barium are correct? 1 2 3 Their reactivity increases with increasing relative atomic mass. The oxidation number exhibited in their stable compounds is +2. On strong heating, their nitrates give off oxygen only. 35 Chlorine is a greenish-yellow gas, bromine is a dark red liquid and iodine is a dark grey solid. What causes these differences in volatility? 1 2 3 the halogen-halogen bond energy the magnitude of the van der Waals’ forces between the molecules the number of electrons in the halogen molecule 36 Which statements about the Haber process for the industrial production of ammonia are correct? 1 2 3 The equilibrium constant Kp increases with pressure. As the temperature increases, the equilibrium constant for the forward reaction becomes smaller. The process is usually carried out at between 450 °C and 550 °C at a pressure of at least 150 atm. 37 Which statements about alkenes are correct? 1 2 3 They are formed when higher alkanes are cracked. They are used as monomers for polymerisation. They are less reactive than alkanes towards electrophiles. © UCLES 2008 9701/01/O/N/08 www.xtremepapers.net 13 38 Which of the following would be suitable for use in a fire extinguisher? 1 2 3 CBrF3 CH3(CH2)5CH2Br HCl 39 During the bromination of methane, the free radical CH• is generated and a possible terminating 3 step of this reaction is the formation of C2H6 by the combination of two free radicals. What could be produced in a terminating step during the bromination of propane? CH3 1 CH3CH2CH2CHCH3 CH3 CH3 2 CH3CHCHCH3 CH3 3 CH3CH2CHCH2CH3 40 The structure of the antioxidant vitamin C is shown in the diagram. HO C O C O C CHCH(OH)CH2OH OH On the basis of this structure, which properties is vitamin C likely to have? 1 2 3 It is soluble in water. It decolourises aqueous bromine rapidly. It reduces Fehling’s reagent. © UCLES 2008 9701/01/O/N/08 www.xtremepapers.net 14 BLANK PAGE 9701/01/O/N/08 www.xtremepapers.net 15 BLANK PAGE 9701/01/O/N/08 www.xtremepapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. 9701/01/O/N/08 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) 9701/11 October/November 2009 1 hour Data Booklet *4953393305* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 16 printed pages. IB09 11_9701_11/FP © UCLES 2009 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 An element X consists of four isotopes. The mass spectrum of X is shown in the diagram. 100 80 relative 60 abundance 40 % 20 0 90 91 92 m/e 93 94 What is the relative atomic mass of X? A 2 91.00 B 91.30 C 91.75 D 92.00 0.200 mol of a hydrocarbon undergo complete combustion to give 35.2 g of carbon dioxide and 14.4 g of water as the only products. What is the molecular formula of the hydrocarbon? A C2H4 B C2H6 C C4H4 D C4H8 © UCLES 2009 9701/11/O/N/09 www.xtremepapers.net 3 3 Use of the Data Booklet is relevant to this question. The graph represents the variation of a property of the Group II elements. property Be What is this property? A B C D 4 ionic radius ionisation energy neutron / proton ratio rate of reaction with water Mg Ca Sr Ba The antidote molecule shown can help to prevent liver damage if someone takes too many paracetamol tablets. x H S H y C H C z H H N H H represents a lone pair What is the order of decreasing size of the bond angles x, y and z? largest A B C D x x y z y z z y smallest z y x x © UCLES 2009 9701/11/O/N/09 [Turn over www.xtremepapers.net 4 5 Which molecule has the largest overall dipole? A Cl C Cl C Cl Cl O C H B H O C Cl C Cl O C O D 6 The first stage in the industrial production of nitric acid from ammonia can be represented by the following equation. 4NH3(g) + 5O2(g) 4NO(g) + 6H2O(g) Using the following standard enthalpy change of formation data, what is the value of the standard enthalpy change, ∆Ho, for this reaction? compound NH3(g) NO(g) H2O(g) A B C D 7 +905.2 kJ mol–1 –105.4 kJ mol–1 –905.2 kJ mol–1 –1274.0 kJ mol–1 ∆Hfo / kJ mol–1 –46.1 +90.3 –241.8 Which conversion involves a reduction of chromium? A B C D CrO 2− → CrO3 4 2 CrO2 − → Cr2O7 − 4 CrO2Cl2 → CrO2 − 4 CrO2Cl2 → Cr2O3 © UCLES 2009 9701/11/O/N/09 www.xtremepapers.net 5 8 The equilibrium N2(g) + O2(g) 2NO(g) ∆H = +180 kJ mol–1 contributes to a series of reactions producing photochemical smog. Which factors would affect the value of Kp of the above equilibrium? change in pressure A B C D     change in temperature     presence or absence of a catalyst     9 PCl5 dissociates as follows. PCl5(g) → PCl3(g) + Cl2(g) The extent of dissociation is 13 % at 160 °C and 100 % at 300 °C. Which pair of statements about this formation of PCl3 is correct? shape of PCl3 molecule A B C D pyramidal pyramidal trigonal trigonal the reaction is endothermic exothermic endothermic exothermic © UCLES 2009 9701/11/O/N/09 [Turn over www.xtremepapers.net 6 10 Four reactions of the type shown are studied at the same temperature. X (g) + Y (g) → Z (g) Which is the correct reaction pathway diagram for the reaction that would proceed most rapidly and with the highest yield? A B energy energy reactant C product reactant D product energy energy reactant product reactant product 11 Photochromic glass, used for sunglasses, darkens when exposed to bright light and becomes more transparent again when the light is less bright. The depth of colour of the glass is related to the concentration of silver atoms. The following reactions are involved. reaction 1 reaction 2 reaction 3 Ag+ + Cl – Ag + Cl Cu+ + Cl → Cu2+ + Cl – Cu2+ + Ag → Cu+ + Ag+ Which statement about these reactions is correct? A B C D Cu+ and Cu2+ ions act as catalysts. Cu+ ions act as an oxidising agent in reaction 2. Reaction 2 is the one in which light is absorbed. Ag+ ions are oxidised in reaction 1. © UCLES 2009 9701/11/O/N/09 www.xtremepapers.net 7 12 The following graph shows the variation of a property of the first 20 elements in the Periodic Table with the atomic number of the element. property 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 atomic number What is the property? A B C D atomic radius first ionisation energy ionic radius melting point 13 Which statement correctly describes what happens when silicon tetrachloride is added to water? A B C D The SiCl4 dissolves to give a neutral solution only. The SiCl4 reacts to give an acidic solution only. The SiCl4 reacts to give a precipitate and an acidic solution. The SiCl4 reacts to give a precipitate and a neutral solution. 14 The oxide and chloride of an element X are separately mixed with water. The two resulting solutions have the same effect on litmus. What is element X? A B C D sodium magnesium aluminium phosphorus © UCLES 2009 9701/11/O/N/09 [Turn over www.xtremepapers.net 8 15 Which graph correctly describes a trend found in the halogen group? [X represents a halogen atom.] A bond length in X2 Cl2 Br2 I2 strength of van der Waals' forces Cl2 B Br2 I2 C boiling point of X2 Cl2 Br2 I2 bond energy of HX D HCl HBr HI 16 During electrolysis of brine in a diaphragm cell, chlorine, hydrogen and sodium hydroxide are produced. What is the molar ratio of these products? chlorine A B C D 1 1 2 2 hydrogen 1 1 1 2 sodium hydroxide 1 2 1 1 17 When sulfur trioxide is manufactured from sulfur dioxide and oxygen, using the Contact process, which condition affects the value of the equilibrium constant, Kc? A B C D adjusting the temperature adjusting the pressure using a catalyst removing SO3 from the equilibrium mixture © UCLES 2009 9701/11/O/N/09 www.xtremepapers.net 9 18 Most modern cars are fitted with three-way catalytic converters in the exhaust system. Which three gases are removed by such a catalytic converter? A B C D carbon monoxide, hydrocarbons, nitrogen oxides carbon monoxide, carbon dioxide, nitrogen oxides carbon monoxide, nitrogen oxides, sulfur dioxide hydrocarbons, nitrogen oxides, sulfur dioxide 19 In an historically famous experiment Wöhler heated ‘inorganic’ ammonium cyanate in the absence of air. The only product of the reaction was ‘organic’ urea, CO(NH2)2. No other products were formed in the reaction. What is the formula of the cyanate ion present in ammonium cyanate? A CNO– B CNO2– C CO– D NO– 20 The drug cortisone has the formula shown. CH2OH CO CH3 OH O CH3 O In addition to those chiral centres marked by an asterisk (*), how many other chiral centres are present in the cortisone molecule? A 0 B 1 C 2 D 3 © UCLES 2009 9701/11/O/N/09 [Turn over www.xtremepapers.net 10 21 The presence of 11-cis retinal, C20H28O, in cells in the eye is important for vision. The structure of retinal includes an aldehyde group, a cyclohexene ring and a long aliphatic side chain, in which a carbon-carbon double bond exists between carbons numbered 11 and 12. Which pair of statements about 11-cis retinal could be correct? total number of >C=C< double bonds arrangement around the adjacent carbons 11 and 12 R1 R2 C H R1 C H H C H R1 C R2 R2 C H R1 C H H C H C R2 A 5 B 5 C 6 D 6 22 What is the least number of carbon atoms in a non-cyclic alkane molecule that has a chiral centre? A 7 B 8 C 9 D 10 23 The following diagram represents the structure of a possible polymer. OH OH OH OH OH OH C H C H C H C H C H C H By which method might this polymer be made? A B C D polymerise ethene followed by hydration polymerise ethene followed by oxidation with cold acidified KMnO4 polymerise 1,2-dichloroethene followed by hydrolysis polymerise 1,2-dichloroethene followed by oxidation with cold acidified KMnO4 © UCLES 2009 9701/11/O/N/09 www.xtremepapers.net 11 24 Sorbic acid is used as a food preservative because it kills fungi and moulds. H C H3C C H H C C H O C OH sorbic acid Sorbic acid will react with • • hydrogen in the presence of a nickel catalyst, bromine in an organic solvent. How many moles of hydrogen and of bromine will be incorporated into one mole of sorbic acid by these reactions? moles of hydrogen A B C D 2 2 3 3 moles of bromine 2 1 22 2 22 1 25 Bromine reacts with ethene to form 1,2-dibromoethane. What is the correct description of the organic intermediate in this reaction? A B C D It has a negative charge. It is a free radical. It is a nucleophile. It is an electrophile. 26 Which equation represents a valid propagation step in the free radical reaction between ethane and chlorine? A B C D C2H6 + Cl • → C2H5Cl + H• C2H5Cl + Cl • → C2H4Cl • + HCl C2H6 + H• → C2H • + HCl 5 C2H5• + Cl • → C2H5Cl © UCLES 2009 9701/11/O/N/09 [Turn over www.xtremepapers.net 12 27 The naturally-occurring molecule civetone is found in a gland of the African civet cat and has been used in perfumery. CH2 H2C H 2C CH HC CH2 H2C H 2C CH2 CH2 civetone CH2 CH2 CH2 CH2 CH2 C O CH2 With which reagent will civetone not react? A B C D 2,4-dinitrophenylhydrazine reagent Fehling’s reagent hydrogen bromide sodium tetrahydridoborate(III) (sodium borohydride) 28 Cyanohydrins can be made from carbonyl compounds by generating CN– ions from HCN in the presence of a weak base. R C R′ O + HCN CN – R C R′ OH CN In a similar reaction, –CH2CO2CH3 ions are generated from CH3CO2CH3 by strong bases. Which compound can be made from an aldehyde and CH3CO2CH3 in the presence of a strong base? A B C D CH3CH(OH)CO2CH3 CH3CO2CH2CH(OH)CH3 CH3CH2CH(OH)CH2CO2CH3 (CH3)2C(OH)CH2CO2CH3 © UCLES 2009 9701/11/O/N/09 www.xtremepapers.net 13 29 The characteristic odour of rum is attributed to the compound 2-ethyl-3-methylbutanoic acid. CH3 C2H5 H 3C C H C H C O OH 2-ethyl-3-methylbutanoic acid Which compound will produce 2-ethyl-3-methylbutanoic acid by heating under reflux with alcoholic sodium cyanide and subsequent acid hydrolysis of the reaction product? CH3 A CH3 CH CH3 B CH3 CH CH3 C CH3 CH CH3 D CH3 CH CH2 CHBr C 2 H5 CH CH2Br CH2Br CH CH3 CH2 CH3 CH2 CHBr CH3 30 The acarid mite releases Iardolure to attract other mites to a host. This chemical can be destroyed by hydrolysis with acid. CH3CH2CH2[CH(CH3)CH2]3CH(CH3)O C O H A simplified formula for lardolure may be written as follows. RCH(CH3)O C O H What are the products of its hydrolysis? A B C D RCH(CH3)CO2H + CH3OH RCH(CH3)CO2H + HCO2H RCH(CH3)OH + CO2 RCH(CH3)OH + HCO2H © UCLES 2009 9701/11/O/N/09 [Turn over www.xtremepapers.net 14 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 A monomer undergoes addition polymerisation. A 1 mol sample of the monomer is completely polymerised. How many moles of polymer might, theoretically, be formed? 1 2 3 1 10–6 1 6.02 × 1023 32 Which physical properties are due to hydrogen bonding between water molecules? 1 2 3 Water has a higher boiling point than H2S. Ice floats on water. The H−O−H bond angle in water is approximately 104°. 33 Which equilibria, in which all species are gaseous, would have equilibrium constants, Kp, with no units? 1 2 3 sulfur dioxide and oxygen in equilibrium with sulfur trioxide hydrogen and iodine in equilibrium with hydrogen iodide carbon monoxide and steam in equilibrium with carbon dioxide and hydrogen © UCLES 2009 9701/11/O/N/09 www.xtremepapers.net 15 34 Why does a mixture of hydrogen gas and bromine gas react together faster at a temperature of 500 K than it does at a temperature of 400 K? 1 2 3 A higher proportion of effective collisions occurs at 500 K. Hydrogen molecules and bromine molecules collide more frequently at 500 K. The activation energy of the reaction is lower at 500 K. 35 A farmer added lime to damp soil, followed by the nitrogenous fertiliser ammonium sulfate. A chemical reaction occurred in the soil. Which substances were formed in this reaction? 1 2 3 sulfuric acid calcium sulfate ammonia 36 Which statements about the reaction of solid sodium bromide with concentrated sulfuric acid are correct? 1 2 3 Hydrogen bromide is a product of the reaction. Sulfuric acid is oxidised to sulfur dioxide. Bromide ions are reduced to bromine. 37 Which statements are true for an SN2 reaction? 1 2 3 One bond is broken as another bond is formed. The formation of a transition state involves the collision of two molecules or ions. A carbon atom in the transition state is bonded, either fully or partially, to five other atoms. 38 The chlorine free radical takes part in the destruction of the ozone layer. Which statements about this free radical are correct? 1 2 3 It is formed by the heterolytic fission of the covalent bond in a chlorine-containing molecule. It has a single unpaired electron. It has the same electron arrangement as a chlorine atom. © UCLES 2009 9701/11/O/N/09 [Turn over www.xtremepapers.net 16 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 39 The diagram shows an experiment. liquid X on mineral wool support silica, alumina or baked clay gas collected gentle heat strong heat trough of water Which processes could be demonstrated by using the above apparatus? 1 2 3 the oxidation of ethanol (the liquid X) the dehydration of ethanol (the liquid X) the cracking of paraffin (the liquid X) 40 A compound has a relative molecular mass of 88 and its molecule contains only four carbon atoms. What could this compound be? 1 2 3 a saturated non-cyclic diol a secondary alcohol containing an aldehyde group a primary alcohol containing a ketone group Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2009 9701/11/O/N/09 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) 9701/12 October/November 2009 1 hour Data Booklet *6243336735* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 16 printed pages. IB09 11_9701_12/FP © UCLES 2009 [Turn over www.xtremepapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 0.200 mol of a hydrocarbon undergo complete combustion to give 35.2 g of carbon dioxide and 14.4 g of water as the only products. What is the molecular formula of the hydrocarbon? A 2 C2H4 B C2H6 C C4H4 D C4H8 Use of the Data Booklet is relevant to this question. The graph represents the variation of a property of the Group II elements. property Be What is this property? A B C D ionic radius ionisation energy neutron / proton ratio rate of reaction with water Mg Ca Sr Ba © UCLES 2009 9701/12/O/N/09 www.xtremepapers.net 3 3 The antidote molecule shown can help to prevent liver damage if someone takes too many paracetamol tablets. x H S H y C H C z H H N H H represents a lone pair What is the order of decreasing size of the bond angles x, y and z? largest A B C D x x y z y z z y smallest z y x x 4 Which molecule has the largest overall dipole? A Cl C Cl C Cl Cl O C H B H O C Cl C Cl O C O D 5 The first stage in the industrial production of nitric acid from ammonia can be represented by the following equation. 4NH3(g) + 5O2(g) 4NO(g) + 6H2O(g) Using the following standard enthalpy change of formation data, what is the value of the standard enthalpy change, ∆Ho, for this reaction? compound NH3(g) NO(g) H2O(g) A B C D +905.2 kJ mol–1 –105.4 kJ mol–1 –905.2 kJ mol–1 –1274.0 kJ mol–1 ∆Hfo / kJ mol–1 –46.1 +90.3 –241.8 © UCLES 2009 9701/12/O/N/09 [Turn over www.xtremepapers.net 4 6 Which conversion involves a reduction of chromium? A B C D 7 CrO 2− → CrO3 4 2 CrO2 − → Cr2O7 − 4 CrO2Cl2 → CrO2 − 4 CrO2Cl2 → Cr2O3 The equilibrium N2(g) + O2(g) 2NO(g) ∆H = +180 kJ mol–1 contributes to a series of reactions producing photochemical smog. Which factors would affect the value of Kp of the above equilibrium? change in pressure A B C D     change in temperature     presence or absence of a catalyst     8 PCl5 dissociates as follows. PCl5(g) → PCl3(g) + Cl2(g) The extent of dissociation is 13 % at 160 °C and 100 % at 300 °C. Which pair of statements about this formation of PCl3 is correct? shape of PCl3 molecule A B C D pyramidal pyramidal trigonal trigonal the reaction is endothermic exothermic endothermic exothermic © UCLES 2009 9701/12/O/N/09 www.xtremepapers.net 5 9 Four reactions of the type shown are studied at the same temperature. X (g) + Y (g) → Z (g) Which is the correct reaction pathway diagram for the reaction that would proceed most rapidly and with the highest yield? A B energy energy reactant C product reactant D product energy energy reactant product reactant product 10 Photochromic glass, used for sunglasses, darkens when exposed to bright light and becomes more transparent again when the light is less bright. The depth of colour of the glass is related to the concentration of silver atoms. The following reactions are involved. reaction 1 reaction 2 reaction 3 Ag+ + Cl – Ag + Cl Cu+ + Cl → Cu2+ + Cl – Cu2+ + Ag → Cu+ + Ag+ Which statement about these reactions is correct? A B C D Cu+ and Cu2+ ions act as catalysts. Cu+ ions act as an oxidising agent in reaction 2. Reaction 2 is the one in which light is absorbed. Ag+ ions are oxidised in reaction 1. © UCLES 2009 9701/12/O/N/09 [Turn over www.xtremepapers.net 6 11 The following graph shows the variation of a property of the first 20 elements in the Periodic Table with the atomic number of the element. property 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 atomic number What is the property? A B C D atomic radius first ionisation energy ionic radius melting point 12 Which statement correctly describes what happens when silicon tetrachloride is added to water? A B C D The SiCl4 dissolves to give a neutral solution only. The SiCl4 reacts to give an acidic solution only. The SiCl4 reacts to give a precipitate and an acidic solution. The SiCl4 reacts to give a precipitate and a neutral solution. 13 The oxide and chloride of an element X are separately mixed with water. The two resulting solutions have the same effect on litmus. What is element X? A B C D sodium magnesium aluminium phosphorus © UCLES 2009 9701/12/O/N/09 www.xtremepapers.net 7 14 Which graph correctly describes a trend found in the halogen group? [X represents a halogen atom.] A bond length in X2 Cl2 Br2 I2 strength of van der Waals' forces Cl2 B Br2 I2 C boiling point of X2 Cl2 Br2 I2 bond energy of HX D HCl HBr HI 15 During electrolysis of brine in a diaphragm cell, chlorine, hydrogen and sodium hydroxide are produced. What is the molar ratio of these products? chlorine A B C D 1 1 2 2 hydrogen 1 1 1 2 sodium hydroxide 1 2 1 1 16 When sulfur trioxide is manufactured from sulfur dioxide and oxygen, using the Contact process, which condition affects the value of the equilibrium constant, Kc? A B C D adjusting the temperature adjusting the pressure using a catalyst removing SO3 from the equilibrium mixture © UCLES 2009 9701/12/O/N/09 [Turn over www.xtremepapers.net 8 17 Most modern cars are fitted with three-way catalytic converters in the exhaust system. Which three gases are removed by such a catalytic converter? A B C D carbon monoxide, hydrocarbons, nitrogen oxides carbon monoxide, carbon dioxide, nitrogen oxides carbon monoxide, nitrogen oxides, sulfur dioxide hydrocarbons, nitrogen oxides, sulfur dioxide 18 In an historically famous experiment Wöhler heated ‘inorganic’ ammonium cyanate in the absence of air. The only product of the reaction was ‘organic’ urea, CO(NH2)2. No other products were formed in the reaction. What is the formula of the cyanate ion present in ammonium cyanate? A CNO– B CNO2– C CO– D NO– 19 The drug cortisone has the formula shown. CH2OH CO CH3 OH O CH3 O In addition to those chiral centres marked by an asterisk (*), how many other chiral centres are present in the cortisone molecule? A 0 B 1 C 2 D 3 © UCLES 2009 9701/12/O/N/09 www.xtremepapers.net 9 20 The presence of 11-cis retinal, C20H28O, in cells in the eye is important for vision. The structure of retinal includes an aldehyde group, a cyclohexene ring and a long aliphatic side chain, in which a carbon-carbon double bond exists between carbons numbered 11 and 12. Which pair of statements about 11-cis retinal could be correct? total number of >C=C< double bonds arrangement around the adjacent carbons 11 and 12 R1 R2 C H R1 C H H C H R1 C R2 R2 C H R1 C H H C H C R2 A 5 B 5 C 6 D 6 21 What is the least number of carbon atoms in a non-cyclic alkane molecule that has a chiral centre? A 7 B 8 C 9 D 10 22 The following diagram represents the structure of a possible polymer. OH OH OH OH OH OH C H C H C H C H C H C H By which method might this polymer be made? A B C D polymerise ethene followed by hydration polymerise ethene followed by oxidation with cold acidified KMnO4 polymerise 1,2-dichloroethene followed by hydrolysis polymerise 1,2-dichloroethene followed by oxidation with cold acidified KMnO4 © UCLES 2009 9701/12/O/N/09 [Turn over www.xtremepapers.net 10 23 Sorbic acid is used as a food preservative because it kills fungi and moulds. H C H3C C H H C C H O C OH sorbic acid Sorbic acid will react with • • hydrogen in the presence of a nickel catalyst, bromine in an organic solvent. How many moles of hydrogen and of bromine will be incorporated into one mole of sorbic acid by these reactions? moles of hydrogen A B C D 2 2 3 3 moles of bromine 2 1 22 2 22 1 24 Bromine reacts with ethene to form 1,2-dibromoethane. What is the correct description of the organic intermediate in this reaction? A B C D It has a negative charge. It is a free radical. It is a nucleophile. It is an electrophile. 25 Which equation represents a valid propagation step in the free radical reaction between ethane and chlorine? A B C D C2H6 + Cl • → C2H5Cl + H• C2H5Cl + Cl • → C2H4Cl • + HCl C2H6 + H• → C2H • + HCl 5 C2H5• + Cl • → C2H5Cl © UCLES 2009 9701/12/O/N/09 www.xtremepapers.net 11 26 The naturally-occurring molecule civetone is found in a gland of the African civet cat and has been used in perfumery. CH2 H2C H 2C CH HC CH2 H2C H 2C CH2 CH2 civetone CH2 CH2 CH2 CH2 CH2 C O CH2 With which reagent will civetone not react? A B C D 2,4-dinitrophenylhydrazine reagent Fehling’s reagent hydrogen bromide sodium tetrahydridoborate(III) (sodium borohydride) 27 Cyanohydrins can be made from carbonyl compounds by generating CN– ions from HCN in the presence of a weak base. R C R′ O + HCN CN – R C R′ OH CN In a similar reaction, –CH2CO2CH3 ions are generated from CH3CO2CH3 by strong bases. Which compound can be made from an aldehyde and CH3CO2CH3 in the presence of a strong base? A B C D CH3CH(OH)CO2CH3 CH3CO2CH2CH(OH)CH3 CH3CH2CH(OH)CH2CO2CH3 (CH3)2C(OH)CH2CO2CH3 © UCLES 2009 9701/12/O/N/09 [Turn over www.xtremepapers.net 12 28 The characteristic odour of rum is attributed to the compound 2-ethyl-3-methylbutanoic acid. CH3 C2H5 H 3C C H C H C O OH 2-ethyl-3-methylbutanoic acid Which compound will produce 2-ethyl-3-methylbutanoic acid by heating under reflux with alcoholic sodium cyanide and subsequent acid hydrolysis of the reaction product? CH3 A CH3 CH CH3 B CH3 CH CH3 C CH3 CH CH3 D CH3 CH CH2 CHBr C 2 H5 CH CH2Br CH2Br CH CH3 CH2 CH3 CH2 CHBr CH3 29 The acarid mite releases Iardolure to attract other mites to a host. This chemical can be destroyed by hydrolysis with acid. CH3CH2CH2[CH(CH3)CH2]3CH(CH3)O C O H A simplified formula for lardolure may be written as follows. RCH(CH3)O C O H What are the products of its hydrolysis? A B C D RCH(CH3)CO2H + CH3OH RCH(CH3)CO2H + HCO2H RCH(CH3)OH + CO2 RCH(CH3)OH + HCO2H © UCLES 2009 9701/12/O/N/09 www.xtremepapers.net 13 30 An element X consists of four isotopes. The mass spectrum of X is shown in the diagram. 100 80 relative 60 abundance 40 % 20 0 90 91 92 m/e 93 94 What is the relative atomic mass of X? A 91.00 B 91.30 C 91.75 D 92.00 © UCLES 2009 9701/12/O/N/09 [Turn over www.xtremepapers.net 14 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Which physical properties are due to hydrogen bonding between water molecules? 1 2 3 Water has a higher boiling point than H2S. Ice floats on water. The H−O−H bond angle in water is approximately 104°. 32 Which equilibria, in which all species are gaseous, would have equilibrium constants, Kp, with no units? 1 2 3 sulfur dioxide and oxygen in equilibrium with sulfur trioxide hydrogen and iodine in equilibrium with hydrogen iodide carbon monoxide and steam in equilibrium with carbon dioxide and hydrogen 33 Why does a mixture of hydrogen gas and bromine gas react together faster at a temperature of 500 K than it does at a temperature of 400 K? 1 2 3 A higher proportion of effective collisions occurs at 500 K. Hydrogen molecules and bromine molecules collide more frequently at 500 K. The activation energy of the reaction is lower at 500 K. 34 A farmer added lime to damp soil, followed by the nitrogenous fertiliser ammonium sulfate. A chemical reaction occurred in the soil. Which substances were formed in this reaction? 1 2 3 sulfuric acid calcium sulfate ammonia 9701/12/O/N/09 © UCLES 2009 www.xtremepapers.net 15 35 Which statements about the reaction of solid sodium bromide with concentrated sulfuric acid are correct? 1 2 3 Hydrogen bromide is a product of the reaction. Sulfuric acid is oxidised to sulfur dioxide. Bromide ions are reduced to bromine. 36 Which statements are true for an SN2 reaction? 1 2 3 One bond is broken as another bond is formed. The formation of a transition state involves the collision of two molecules or ions. A carbon atom in the transition state is bonded, either fully or partially, to five other atoms. 37 The chlorine free radical takes part in the destruction of the ozone layer. Which statements about this free radical are correct? 1 2 3 It is formed by the heterolytic fission of the covalent bond in a chlorine-containing molecule. It has a single unpaired electron. It has the same electron arrangement as a chlorine atom. 38 The diagram shows an experiment. liquid X on mineral wool support silica, alumina or baked clay gas collected gentle heat strong heat trough of water Which processes could be demonstrated by using the above apparatus? 1 2 3 the oxidation of ethanol (the liquid X) the dehydration of ethanol (the liquid X) the cracking of paraffin (the liquid X) © UCLES 2009 9701/12/O/N/09 [Turn over www.xtremepapers.net 16 39 A compound has a relative molecular mass of 88 and its molecule contains only four carbon atoms. What could this compound be? 1 2 3 a saturated non-cyclic diol a secondary alcohol containing an aldehyde group a primary alcohol containing a ketone group 40 A monomer undergoes addition polymerisation. A 1 mol sample of the monomer is completely polymerised. How many moles of polymer might, theoretically, be formed? 1 2 3 1 10–6 6.02 × 1023 1 Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2009 9701/12/O/N/09 www.xtremepapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/11 October/November 2010 1 hour *6961637670* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 15 printed pages and 1 blank page. IB10 11_9701_11/3RP © UCLES 2010 [Turn over www.XtremePapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 Every year millions of tonnes each of chlorine and sodium hydroxide are manufactured by the electrolysis of brine using a ‘diaphragm cell’. What is the purpose of the diaphragm in such a cell? A B C D 2 to prevent chlorine gas escaping into the factory to prevent the build up of pressure in the electrolysis cell to provide a large surface area of electrode to stop the products of electrolysis from reacting together A simple ion X+ contains eight protons. What is the electronic configuration of X+? A B C D 1s2 1s2 1s2 1s2 2s1 2s2 2s2 2s2 2p6 2p3 2p5 2p7 3 Equations involving four enthalpy changes are shown. Na(g) → Na+(g) + e– ∆H = W Na(g) → Na2+(g) + 2e– ∆H = X Na(s) → Na(g) ∆H = Y Na(s) → Na2+(g) + 2e– ∆H = Z What is the second ionisation energy of sodium? A 4 2W B X–W C Y–W D Z–Y Sulfur dioxide, SO2, is added to wines to prevent oxidation of ethanol by air. To determine the amount of SO2, a sample of wine is titrated with iodine, I2. In this reaction, one mole of SO2 is oxidised by one mole of I2. What is the change in oxidation number of sulfur in this reaction? A +2 to +4 B +2 to +6 C +4 to +5 D +4 to +6 © UCLES 2010 9701/11/O/N/10 www.XtremePapers.net 3 5 Use of the Data Booklet is relevant to this question. Nickel makes up 20 % of the total mass of a coin. The coin has a mass of 10.0 g. How many nickel atoms are in the coin? A 6 2.05 × 1022 B 4.30 × 1022 C 1.03 × 1023 D 1.20 × 1024 Which ion has more electrons than protons and more protons than neutrons? 2 [H = 1 H ; D = 1 H ; O = 16 O] 1 8 A D– B H3O+ C OD– D OH– 7 Organic nitrates in photochemical smog can cause breathing difficulties. The diagram shows an example of an organic nitrate molecule. H H 1 3 C H C 2 O O O NO2 What is the correct order of the bond angles shown in ascending order (smallest first)? A 1→2→3 B 2→1→3 C 3→1→2 D 3→2→1 © UCLES 2010 9701/11/O/N/10 [Turn over www.XtremePapers.net 4 8 Enthalpy changes of combustion can be used to determine enthalpy changes of formation. The following equation represents the enthalpy change of formation of butane. 4C(s) + 5H2(g) → C4H10(g) By using the following standard enthalpy of combustion data, what is the value of the standard enthalpy change of formation, , for this reaction? compound carbon hydrogen butane A B C D 9 –5883 kJ mol–1 –129 kJ mol–1 +129 kJ mol–1 +2197 kJ mol–1 o –394 –286 –2877 In a calorimetric experiment 1.60 g of a fuel is burnt. 45 % of the energy released is absorbed by 200 g of water whose temperature rises from 18 °C to 66 °C. The specific heat capacity of water is 4.2 J g–1 K–1. What is the total energy released per gram of fuel burnt? A 25 200 J B 56 000 J C 89 600 J D 143 360 J 10 The value of the equilibrium constant, Kc, for the reaction to form ethyl ethanoate from ethanol and ethanoic acid is 4.0 at 60 °C. C2H5OH + CH3CO2H CH3CO2C2H5 + H2O When 1.0 mol of ethanol and 1.0 mol of ethanoic acid are allowed to reach equilibrium at 60 °C, what is the number of moles of ethyl ethanoate formed? A 1 3 B 2 3 C 1 4 D 3 4 11 Which equation represents the change corresponding to the enthalpy change of atomisation of iodine? A B C D 1 I (g) 2 2 → I(g) I2(g) → 2I(g) 1 I (s) 2 2 → I(g) I2(s) → 2I(g) © UCLES 2010 9701/11/O/N/10 www.XtremePapers.net 5 12 Camphor is a white solid which was used to make the early plastic celluloid. Camphor contains the same percentage by mass of hydrogen and oxygen. What is the molecular formula of camphor? A C10H6O6 B C10H8O C C10H16O D C10H10O2 13 Why is the first ionisation energy of phosphorus greater than the first ionisation energy of silicon? A B C D A phosphorus atom has one more proton in its nucleus. The atomic radius of a phosphorus atom is greater. The outer electron in a phosphorus atom is more shielded. The outer electron in a phosphorus atom is paired. 14 When magnesium nitrate, Mg(NO3)2.7H2O, is heated, which three gases are given off? A B C D dinitrogen oxide, oxygen, water vapour hydrogen, nitrogen, oxygen hydrogen, nitrogen dioxide, oxygen nitrogen dioxide, oxygen, water vapour 15 Ammonium sulfate in nitrogenous fertilisers in the soil can be slowly oxidised by air producing sulfuric acid, nitric acid and water. How many moles of oxygen gas are needed to oxidise completely one mole of ammonium sulfate? A 1 B 2 C 3 D 4 16 Chile saltpetre, NaNO3, contains sodium iodide as an impurity. Aqueous silver nitrate is added to an aqueous solution of Chile saltpetre. Concentrated aqueous ammonia is then added. Which observations are made? with acidified silver nitrate A B C D no precipitate no precipitate precipitate forms precipitate forms with concentrated aqueous ammonia no further reaction precipitate forms precipitate dissolves precipitate remains © UCLES 2010 9701/11/O/N/10 [Turn over www.XtremePapers.net 6 17 Which statement describes the halogens chlorine, bromine and iodine? A B C D Their bond energies decrease with increasing proton number. Their first ionisation energies increase with increasing proton number. They are all coloured gases at room temperature. They are all good reducing agents. 18 Sulfur dioxide is used to bleach wood pulp in the production of paper. It is also used as an additive in the production of jam and marmalade, often in the form of sulfite compounds. When it is present in quantities greater than 10 mg / kg it is required to be listed as an ingredient of the jam. Why is sulfur dioxide added to jam? A B C D 19 It is a bleaching agent and removes the undesirable colours from the fruit used in the jam. It is a preservative that destroys unwanted bacteria and enzymes. It is a reducing agent and removes the acids that give the jam a sharp taste. It is an acidic gas and maintains the pH of the jam at a suitable value to give it a sharp taste. Which property of beryllium and its compounds is typical of the elements below it in Group II? A B C D Be does not react with hot water. BeCl2 is covalent. Be(NO3)2 produces BeO on thermal decomposition. BeO dissolves in alkalis. 20 One of the characteristics of addition polymerisation is that the empirical formulae of the polymer and of its monomer are the same. The absorbent material in babies’ disposable nappies is made from the addition polymer shown. CH2 CH CH2 CH CH2 CH CO2H CO2H CO2H From which monomer could this addition polymer be obtained? A B C D CH3CH(OH)CO2H HOCH2CH2CO2H H2C=CHCO2H HO2CCH=CHCO2H © UCLES 2010 9701/11/O/N/10 www.XtremePapers.net 7 21 Compound X reacts with ethanoic acid in the presence of an H+ catalyst to produce the compound below. O H 3C C H C H H C H O O C CH3 What is the molecular formula of compound X? A C2H6O2 B C2H6O3 C C4H8O D C4H8O2 22 A compound Y has all of the properties below. • • • It is a liquid at 25 °C. It mixes completely with water. It reacts with aqueous sodium hydroxide. What could Y be? A B C D ethanoic acid ethanol ethene ethyl ethanoate 23 Tartaric acid is present in some wines. It may be synthesised in the laboratory in two steps. step 1 OHCCHO intermediate step 2 HO2CCH(OH)CH(OH)CO2H tartaric acid Which reagents could be used for this synthesis? step 1 A B C D HCl (aq) HCN, NaCN(aq/alcoholic) H2SO4(aq) KCN(aq/alcoholic) step 2 HCN(g) H2SO4(aq) K2Cr2O7 / H2SO4(aq) K2Cr2O7 / H2SO4(aq) © UCLES 2010 9701/11/O/N/10 [Turn over www.XtremePapers.net 8 24 Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A B C D butan-1-ol butan-2-ol 2-methylpropan-1-ol 2-methylpropan-2-ol 25 Limonene is an oil formed in the peel of citrus fruits. CH3 C CH2 CH3 limonene Which product is formed when an excess of bromine, Br2(l), reacts with limonene at room temperature in the dark? A CH3 C CH2 Br B CH3 C CH2 CH3 C Br C CH2Br CH3 D Br C CH2Br Br CH3 CH3 Br CH3 CH3 Br Br © UCLES 2010 9701/11/O/N/10 www.XtremePapers.net 9 26 Lactic acid occurs naturally, for example in sour milk. H H H C H O C H lactic acid C O H O What is a property of lactic acid? A B C D It decolourises aqueous bromine rapidly. It is insoluble in water. It reduces Fehling’s reagent. Two molecules react with each other in the presence of a strong acid. 27 Which compound would undergo nucleophilic addition? A B C D bromoethane, C2H5Br ethanal, CH3CHO ethane, C2H6 ethene, C2H4 28 Which compound undergoes an SN1 substitution reaction? A B CH3CH2CH2Br (CH3)3CCH2I CH3 Cl C D CH2=CHCl © UCLES 2010 9701/11/O/N/10 [Turn over www.XtremePapers.net 10 29 The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic rubber. H C H C CH3 CH3 In addition to 2-methylpropene there are x other isomers of C4H8, structural or otherwise, which contain a double bond. What is the value of x? A 1 B 2 C 3 D 4 30 Which environmental problem is not made worse by the release of oxides of nitrogen from car engines? A B C D acidification of lakes corrosion of buildings photochemical smog the hole in the ozone layer © UCLES 2010 9701/11/O/N/10 www.XtremePapers.net 11 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Ethanol is manufactured by reacting ethene gas and steam in the presence of phosphoric(V) acid. C2H4(g) + H2O(g) C2H5OH(g) ∆H = –45 kJ mol–1 The reaction is carried out at 570 K and 60 atm. What would be the consequences of carrying out the reaction at the same temperature but at a pressure of 200 atm? 1 2 3 The manufacturing costs would increase. The maximum yield at equilibrium would be higher. The reaction would proceed at a faster rate. © UCLES 2010 9701/11/O/N/10 [Turn over www.XtremePapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 32 The diagram represents the Boltzmann distribution of molecular energies at a given temperature. proportion of molecules energy Which of the factors that affect the rate of a reaction can be explained using such a Boltzmann distribution? 1 2 3 increasing the concentration of reactants increasing the temperature the addition of a catalyst 33 Which types of intermolecular forces can exist between adjacent urea molecules? O C H 2N urea NH2 1 2 3 hydrogen bonding permanent dipole-dipole forces temporary induced dipole-dipole forces © UCLES 2010 9701/11/O/N/10 www.XtremePapers.net 13 34 Samples of calcium and barium are separately added to beakers of cold water containing a few drops of litmus solution. Which observations will be made with only the calcium and not with the barium? 1 2 3 A white suspension appears in the water. The solution turns blue. A gas is evolved. 35 Disproportionation is the term used to describe a reaction in which a reactant is simultaneously both oxidised and reduced. To which incomplete equations does the term disproportionation apply? 1 2 3 Cl2(g) + 2OH–(aq) → H2O(l) + Cl –(aq) + …… 3Cl2(g) + 6OH–(aq) → 3H2O(l) + ClO3–(aq) + …… 2NO2(g) + H2O(l) → HNO3(aq) + …… 36 Element X is a solid. It occurs as a contaminant of carbonaceous fuels. Its oxide Y is formed in car engines. Further oxidation of Y to Z can occur in the atmosphere. Which statements about Y and Z are correct? 1 2 3 Molecule Y has lone pairs of electrons. The atmospheric oxidation of Y to Z is a catalysed reaction. Y is a colourless gas. © UCLES 2010 9701/11/O/N/10 [Turn over www.XtremePapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 37 The diagram shows the structure of the naturally-occurring molecule cholesterol. H 3C CH3 CH3 H H H HO H cholesterol Which statements about cholesterol are correct? 1 2 3 The molecule contains a secondary alcohol group. The molecule contains two π bonds. All carbon atoms in the four rings lie in the same plane. 38 Glyceraldehyde, HOCH2CH(OH)CHO, is formed during photosynthesis, and contains a chiral carbon atom. Which reagents will react with glyceraldehyde to produce an organic product without a chiral carbon atom? 1 2 3 warmed acidified K2Cr2O7 NaBH4 Tollens’ reagent © UCLES 2010 9701/11/O/N/10 www.XtremePapers.net 15 39 An organic compound decolourises aqueous bromine and reacts with sodium to produce hydrogen. Which molecular formula could represent this compound? 1 2 3 C3H6O C3H4O2 C3H8O 40 Textiles for use in aircraft are treated with a finish containing a halogenoalkane. What is the reason for this? 1 2 3 The textile burns less easily, improving safety. The fabric forms hydrogen bonds to water more readily, making the fabric easier to wash. The halogenoalkane undergoes addition polymerisation, stiffening the fabric. © UCLES 2010 9701/11/O/N/10 www.XtremePapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2010 9701/11/O/N/10 www.XtremePapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/12 October/November 2010 1 hour *2899448619* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 16 printed pages. IB10 11_9701_12/4RP © UCLES 2010 [Turn over www.XtremePapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 The ability of an atom in a covalent bond to attract electrons to itself is called its electronegativity. The greater the difference between the electronegativities of the two atoms in the bond, the more polar is the bond. Which pair will form the most polar covalent bond between the atoms? A B C D 2 chlorine and bromine chlorine and iodine fluorine and chlorine fluorine and iodine Which diagram correctly represents the Boltzmann distribution of molecular energies at two temperatures T1 and T2, where T1 = 300 K and T2 = 310 K? A T1 T2 proportion of molecules proportion of molecules T1 T2 B 0 molecular energy C T2 0 molecular energy D T2 T1 proportion of molecules proportion of molecules T1 0 molecular energy 0 molecular energy © UCLES 2010 9701/12/O/N/10 www.XtremePapers.net 3 3 The table gives the radii, in pm, of some ions. [1 pm = 10–12 m] ion Na+ Mg2+ Cs+ Cl – O2– radii 102 72 167 181 140 Caesium chloride, CsCl, has a different lattice structure from both sodium chloride, NaCl, and magnesium oxide, MgO. CsCl lattice NaCl and MgO lattice Which factor appears to determine the type of lattice for these three compounds? A B C D the charge on the cation the ratio of the ionic charges the ratio of the ionic radii the sum of the ionic charges © UCLES 2010 9701/12/O/N/10 [Turn over www.XtremePapers.net 4 4 Methanol may be prepared by the reaction between carbon monoxide and hydrogen. CO(g) + 2H2(g) → CH3OH(g) The relevant average bond energies are given below. E(C≡O) 1077 kJ mol–1 E(C–O) E(C–H) E(H–H) E(O–H) What is the enthalpy change of this reaction? A B C D 5 –537 kJ mol–1 –101 kJ mol–1 +101 kJ mol–1 +537 kJ mol–1 360 kJ mol–1 410 kJ mol–1 436 kJ mol–1 460 kJ mol–1 Which solid has a simple molecular lattice? A B C D calcium fluoride nickel silicon(IV) oxide sulfur 6 The reaction pathway diagram below illustrates the energies of reactants, products and the transition state of a reaction. E1 transition state energy E2 reactants E3 products reaction coordinate Which expression represents the activation energy of the forward reaction? A E1 – E 2 B E1 – E 3 C E2 – E 3 D (E1 – E2) – (E2 – E3) © UCLES 2010 9701/12/O/N/10 www.XtremePapers.net 5 7 Flask X contains 5 dm3 of helium at 12 kPa pressure and flask Y contains 10 dm3 of neon at 6 kPa pressure. If the flasks are connected at constant temperature, what is the final pressure? A 8 8 kPa B 9 kPa C 10 kPa D 11 kPa Use of the Data Booklet is relevant to this question. The enthalpy change of formation, ∆Hf, of hydrated calcium ions is the enthalpy change of the following reaction. Ca(s) + aq – 2e– → Ca2+(aq) The following enthalpy changes are not quoted in the Data Booklet. Ca(s) → Ca(g) Ca2+(g) + aq → Ca2+(aq) ∆Ha = 177 kJ mol–1 ∆Hhyd = –1565 kJ mol–1 What is the enthalpy change of formation of hydrated calcium ions? A B C D 9 –1388 kJ mol–1 –798 kJ mol–1 –238 kJ mol–1 +352 kJ mol–1 The following equilibrium is set up in a mixture of concentrated nitric and sulfuric acids. HNO3 + H2SO4 H2NO3+ + HSO4– Which row correctly describes the behaviour of each substance in the equilibrium mixture? HNO3 A B C D acid acid base base H2SO4 acid base acid acid H2NO3+ base base acid base HSO4– base acid base acid 10 Which molecule or structure does not contain three atoms bonded at an angle between 109° and 110°? A B C D ethanoic acid graphite propane silicon(IV) oxide 9701/12/O/N/10 © UCLES 2010 [Turn over www.XtremePapers.net 6 11 A dimer, X, is stable when solid but a dynamic equilibrium is set up in solution. X(aq) 2Y(aq) A solution of X has an initial concentration of 0.50 mol dm–3. When equilibrium has been reached [X(aq)] has fallen to 0.25 mol dm–3. The changes in [X(aq)] and [Y(aq)] are plotted against time until equilibrium is reached. The value of Kc is then calculated. Which graph and value for Kc are correct? graph 0.5 0.4 A concentration 0.3 / mol dm–3 0.2 0.1 0 0 0.5 0.4 B concentration 0.3 / mol dm–3 0.2 0.1 0 0 0.5 0.4 C concentration 0.3 / mol dm–3 0.2 0.1 0 0 0.5 0.4 D concentration 0.3 / mol dm–3 0.2 0.1 0 0 time Y time Y time Y X time Y X Kc / mol dm–3 1 2 X 1 X 2 © UCLES 2010 9701/12/O/N/10 www.XtremePapers.net 7 12 Equimolar quantities of magnesium carbonate and strontium carbonate are separately heated to bring about complete thermal decomposition. The minimum temperature for this to occur is called Td. The cold residues are separately added to equal volumes of water and the change in pH is measured. The change in pH is called ∆pH. Which metal has the higher value of Td, and the greater value of ∆pH? Td A B C D Mg Mg Sr Sr ∆pH Mg Sr Mg Sr 13 In aqueous solution, the acid HIO disproportionates according to the following equation where m, n, p and q are simple whole numbers in their lowest ratios. mHIO → nI2 + pHIO3 + qH2O This equation can be balanced using oxidation numbers. What are the values for n and p? n A B C D 1 2 4 4 p 2 1 1 2 14 Use of the Data Booklet is relevant to this question. Which mass of solid residue can be obtained from the thermal decomposition of 4.10 g of anhydrous calcium nitrate? A 0.70 g B 1.00 g C 1.40 g D 2.25 g 15 Which statement explains the observation that magnesium hydroxide dissolves in aqueous ammonium chloride, but not in aqueous sodium chloride? A B C D The ionic radius of the NH4+ ion is similar to that of Mg2+ but not that of Na+. NH4Cl dissociates less fully than NaCl. The Na+ and Mg2+ ions are isoelectronic (have the same number of electrons). The NH4+ ion can donate a proton. [Turn over © UCLES 2010 9701/12/O/N/10 www.XtremePapers.net 8 16 What happens when chlorine is bubbled through aqueous potassium iodide? A B C D Chlorine is oxidised to chlorate(V) ions. Chlorine is oxidised to chloride ions. Iodide ions are oxidised to iodine. There is no observable reaction. 17 Strontium metal can be obtained by the electrolysis of molten strontium bromide, SrBr2, using the apparatus shown in the diagram. steel cathode atmosphere of argon graphite anode molten strontium molten strontium bromide heat Why is an atmosphere of argon used around the cathode? A B C D A thin film of a compound of strontium and argon forms on the surface protecting the freshly formed metal. The argon keeps the strontium molten. The argon stops the molten strontium rising too high in the tube. Without the argon, strontium oxide would form in the air. 18 Which statement about bromine is correct? A B C D Bromine is insoluble in non-polar solvents. Bromine vapour is more dense than air. Bromine will not vapourise significantly under normal conditions. Gaseous bromine is purple. © UCLES 2010 9701/12/O/N/10 www.XtremePapers.net 9 19 Concentrated sulfuric acid reacts with both solid sodium chloride at room temperature and with solid sodium iodide at room temperature. Which row correctly describes how concentrated sulfuric acid behaves in each of these reactions? with sodium chloride A B C D as an oxidising agent only as a strong acid and as an oxidising agent as a strong acid only as a strong acid only with sodium iodide as an oxidising agent only as a strong acid only as a strong acid and as an oxidising agent as a strong acid only 20 How many structural isomers are there of trichloropropane, C3H5Cl 3? A 3 B 4 C 5 D 6 21 Nine compounds have molecular formula C4H8Br2. Which compound may be synthesised from an alkene by an addition reaction? A B C D 1,1-dibromobutane 1,2-dibromobutane 1,3-dibromobutane 1,3-dibromomethylpropane 22 When ethanal, CH3CHO, reacts with HCN and the organic product is hydrolysed by aqueous acid, organic compound Y is formed. When propanal, C2H5CHO, is heated under reflux with acidified potassium dichromate(VI), organic compound Z is formed. What is the difference in relative molecular mass of compounds Y and Z? A 12 B 14 C 16 D 17 23 Which sequence of reagents may be used in the laboratory to convert propan-1-ol into 2-bromopropane? A B C D concentrated sulfuric acid, followed by bromine concentrated sulfuric acid, followed by hydrogen bromide ethanolic sodium hydroxide, followed by bromine ethanolic sodium hydroxide, followed by hydrogen bromide © UCLES 2010 9701/12/O/N/10 [Turn over www.XtremePapers.net 10 24 Esters are frequently used as solvents and as flavouring agents in fruit drinks and confectionery. An ester C8H12Br2O4 can be prepared in low yield by the reaction shown. CH3C(Br)(CH2Br)CO2H + (CH3)2C(OH)CO2H ⇌ C8H12Br2O4 + H2O What is the structural formula of the ester C8H12Br2O4? A B C D CH3C(Br)(CH2Br)CO2C(CH3)2CO2H CH3C(Br)(CH2Br)CO2C(OH)(CH3)CO2CH3 CH3C(Br)(CH3)CO2C(CH3)2CO2CH2Br (CH3)2C(Br)C(CO2H)(CH2Br)CO2CH3 25 Many, but not all, organic reactions need to be heated before reaction occurs. Which reaction occurs at a good rate at room temperature (20 °C)? A B C D C10H22 → C8H18 + C2H4 CH3CH2CH2Br + NH3 → CH3CH2CH2NH2 + HBr CH3CH2OH + KBr → CH3CH2Br + KOH (CH3)2CO + H2NNHC6H3(NO2)2 → (CH3)2C=NNHC6H3(NO2)2 + H2O 26 Which pair of reagents will take part in a redox reaction? A B C D CH3CH2OH + concentrated H2SO4 CH3CHO + Tollens’ reagent CH3CO2C2H5 + dilute H2SO4 CH3COCH3 + Fehling’s solution © UCLES 2010 9701/12/O/N/10 www.XtremePapers.net 11 27 Part of the structure of strobilurin, a fungicide, is shown. R and R' are inert groups. O OCH3 R' R If strobilurin is first warmed with aqueous sulfuric acid, and its product then treated with hydrogen in the presence of a palladium catalyst, what could be the structure of the final product? A O OH R' R R B HO OCH3 R' C OH OH R' R R D O OH R' OH OH 28 Fluoroalkenes are used to make polymers such as poly(vinyl)fluoride (PVF). PVF is used to make non-flammable interiors for aircraft. The diagram shows the repeat unit of the polymer PVF. H C H H C F What is the skeletal formula of the monomer of PVF? H A H H F B F F C D F © UCLES 2010 9701/12/O/N/10 [Turn over www.XtremePapers.net 12 29 CH3CH2COCH2CH3 reacts with hydrogen cyanide to form a cyanohydrin. Which feature applies to the product? A B C D It has one chiral centre. It is formed by electrophilic addition. It is formed via a C–OH intermediate. Its formation requires the use of cyanide ions as a catalyst. 30 Which of the compounds shown have chiral carbon atoms? 1 2 3 OH CH3 CH3 CH3 CH3 4 O OH A B C D 1, 2, 3 and 4 1 and 4 only 2 and 3 only 2, 3 and 4 only © UCLES 2010 9701/12/O/N/10 www.XtremePapers.net 13 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 When ammonia, NH3, is produced in a school or college laboratory, it is usually dried before being collected. Which drying agents may be used to dry ammonia? 1 2 3 calcium oxide, CaO phosphorus(V) oxide, P4O10 concentrated sulfuric acid, H2SO4 32 Zirconium, Zr, proton number 40, is a metal which is used in corrosion-resistant alloys. Zirconium metal is extracted from the oxide ZrO2 by the following sequence of reactions. reaction 1 reaction 2 ZrO2 + 2Cl 2 + 2C → ZrCl 4 + 2CO ZrCl 4 + 2Mg → Zr + 2MgCl 2 Which statements about this extraction process are correct? 1 2 3 Carbon in reaction 1 behaves as a reducing agent. Magnesium in reaction 2 behaves as a reducing agent. Chlorine in reaction 1 behaves as a reducing agent. 33 Which statements about covalent bonds are correct? 1 2 3 A triple bond consists of one π bond and two σ bonds. The electron density in a σ bond is highest along the axis between the two bonded atoms. A π bond restricts rotation about the σ bond axis. © UCLES 2010 9701/12/O/N/10 [Turn over www.XtremePapers.net 14 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 34 A student puts 10 cm3 of 0.100 mol dm–3 sulfuric acid into one test-tube and 10 cm3 of 0.100 mol dm–3 ethanoic acid into another test-tube. He then adds 1.0 g (an excess) of magnesium ribbon to each test-tube and takes suitable measurements. Both acids have the same starting temperature. Neither reaction is complete after 2 minutes, but both are complete after 20 minutes. Which statements are correct? 1 2 3 After 2 minutes, the sulfuric acid is at a higher temperature than the ethanoic acid. After 2 minutes, the sulfuric acid has produced more gas than the ethanoic acid. After 20 minutes, the sulfuric acid has produced more gas than the ethanoic acid. 35 In which ways are the main reactions in the Haber and Contact processes similar? 1 2 3 A higher yield is favoured by higher pressures. The reaction is a redox process. The forward reaction is exothermic. 36 A car burning lead-free fuel has a catalytic converter fitted to its exhaust. On analysis its exhaust gases are shown to contain small quantities of nitrogen oxides. Which modifications would result in lower exhaust concentrations of nitrogen oxides? 1 2 3 an increase in the surface area of the catalyst in the converter an increase in the rate of flow of the exhaust gases through the converter a much higher temperature of combustion in the engine © UCLES 2010 9701/12/O/N/10 www.XtremePapers.net 15 37 The diagram shows a compound present in smoke from burning garden waste. H C H H C H C O Which reagents would undergo a colour change on reaction with this compound? 1 2 3 aqueous bromine Fehling’s reagent warm acidified K2Cr2O7 38 Organic acids and alcohols react together to form esters. Which pairs of compounds could produce a product of molecular formula C4H6O4? 1 2 3 CH3CO2H and C2H5OH HCO2H and HOCH2CH2OH HO2CCO2H and CH3OH 39 Use of the Data Booklet is relevant for this question. In an organic synthesis, a 62 % yield of product is achieved. Which of these conversions are consistent with this information? 1 2 3 74.00g of butan-2-ol → 44.64 g of butanone 74.00g of butan-1-ol → 54.56 g of butanoic acid 74.00g of 2-methylpropan-1-ol → 54.56 g of 2-methylpropanoic acid © UCLES 2010 9701/12/O/N/10 [Turn over www.XtremePapers.net 16 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 40 A reaction pathway diagram is shown. energy reaction pathway Which reactions would have such a profile? 1 2 3 (CH3)3CBr + NaOH → (CH3)3COH + NaBr CH3CH2Br + NaOH → CH3CH2OH + NaBr (CH3)3CCH2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2010 9701/12/O/N/10 www.XtremePapers.net UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS General Certificate of Education Advanced Subsidiary Level and Advanced Level CHEMISTRY Paper 1 Multiple Choice Additional Materials: Multiple Choice Answer Sheet Soft clean eraser Soft pencil (type B or HB is recommended) Data Booklet 9701/13 October/November 2010 1 hour *6196456143* READ THESE INSTRUCTIONS FIRST Write in soft pencil. Do not use staples, paper clips, highlighters, glue or correction fluid. Write your name, Centre number and candidate number on the Answer Sheet in the spaces provided unless this has been done for you. There are forty questions on this paper. Answer all questions. For each question there are four possible answers A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the separate Answer Sheet. Read the instructions on the Answer Sheet very carefully. Each correct answer will score one mark. A mark will not be deducted for a wrong answer. Any rough working should be done in this booklet. This document consists of 13 printed pages and 3 blank pages. IB10 11_9701_13/RP © UCLES 2010 [Turn over www.XtremePapers.net 2 Section A For each question there are four possible answers, A, B, C, and D. Choose the one you consider to be correct. 1 A simple ion X+ contains eight protons. What is the electronic configuration of X+? A B C D 2 1s2 1s2 1s2 1s2 2s1 2s2 2s2 2s2 2p6 2p3 2p5 2p7 Equations involving four enthalpy changes are shown. Na(g) → Na+(g) + e– ∆H = W Na(g) → Na2+(g) + 2e– ∆H = X Na(s) → Na(g) ∆H = Y Na(s) → Na2+(g) + 2e– ∆H = Z What is the second ionisation energy of sodium? A 3 2W B X–W C Y–W D Z–Y Which ion has more electrons than protons and more protons than neutrons? 2 [H = 1 H ; D = 1 H ; O = 16 O] 1 8 A D– B H3O+ C OD– D OH– 4 Sulfur dioxide, SO2, is added to wines to prevent oxidation of ethanol by air. To determine the amount of SO2, a sample of wine is titrated with iodine, I2. In this reaction, one mole of SO2 is oxidised by one mole of I2. What is the change in oxidation number of sulfur in this reaction? A +2 to +4 B +2 to +6 C +4 to +5 D +4 to +6 5 Use of the Data Booklet is relevant to this question. Nickel makes up 20 % of the total mass of a coin. The coin has a mass of 10.0 g. How many nickel atoms are in the coin? A 2.05 × 1022 B 4.30 × 1022 C 1.03 × 1023 D 1.20 × 1024 © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net 3 6 Organic nitrates in photochemical smog can cause breathing difficulties. The diagram shows an example of an organic nitrate molecule. H H 1 3 C H C 2 O O O NO2 What is the correct order of the bond angles shown in ascending order (smallest first)? A 7 1→2→3 B 2→1→3 C 3→1→2 D 3→2→1 Every year millions of tonnes each of chlorine and sodium hydroxide are manufactured by the electrolysis of brine using a ‘diaphragm cell’. What is the purpose of the diaphragm in such a cell? A B C D to prevent chlorine gas escaping into the factory to prevent the build up of pressure in the electrolysis cell to provide a large surface area of electrode to stop the products of electrolysis from reacting together 8 Which statement describes the halogens chlorine, bromine and iodine? A B C D Their bond energies decrease with increasing proton number. Their first ionisation energies increase with increasing proton number. They are all coloured gases at room temperature. They are all good reducing agents. 9 Chile saltpetre, NaNO3, contains sodium iodide as an impurity. Aqueous silver nitrate is added to an aqueous solution of Chile saltpetre. Concentrated aqueous ammonia is then added. Which observations are made? with acidified silver nitrate A B C D no precipitate no precipitate precipitate forms precipitate forms with concentrated aqueous ammonia no further reaction precipitate forms precipitate dissolves precipitate remains © UCLES 2010 9701/13/O/N/10 [Turn over www.XtremePapers.net 4 10 The value of the equilibrium constant, Kc, for the reaction to form ethyl ethanoate from ethanol and ethanoic acid is 4.0 at 60 °C. C2H5OH + CH3CO2H CH3CO2C2H5 + H2O When 1.0 mol of ethanol and 1.0 mol of ethanoic acid are allowed to reach equilibrium at 60 °C, what is the number of moles of ethyl ethanoate formed? A 1 3 B 2 3 C 1 4 D 3 4 11 Enthalpy changes of combustion can be used to determine enthalpy changes of formation. The following equation represents the enthalpy change of formation of butane. 4C(s) + 5H2(g) → C4H10(g) By using the following standard enthalpy of combustion data, what is the value of the standard enthalpy change of formation, , for this reaction? compound carbon hydrogen butane A B C D –5883 kJ mol–1 –129 kJ mol–1 +129 kJ mol–1 +2197 kJ mol–1 o –394 –286 –2877 12 In a calorimetric experiment 1.60 g of a fuel is burnt. 45 % of the energy released is absorbed by 200 g of water whose temperature rises from 18 °C to 66 °C. The specific heat capacity of water is 4.2 J g–1 K–1. What is the total energy released per gram of fuel burnt? A 25 200 J B 56 000 J C 89 600 J D 143 360 J 13 Which equation represents the change corresponding to the enthalpy change of atomisation of iodine? A B C D 1 I (g) 2 2 → I(g) I2(g) → 2I(g) 1 I (s) 2 2 → I(g) I2(s) → 2I(g) © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net 5 14 Camphor is a white solid which was used to make the early plastic celluloid. Camphor contains the same percentage by mass of hydrogen and oxygen. What is the molecular formula of camphor? A C10H6O6 B C10H8O C C10H16O D C10H10O2 15 Ammonium sulfate in nitrogenous fertilisers in the soil can be slowly oxidised by air producing sulfuric acid, nitric acid and water. How many moles of oxygen gas are needed to oxidise completely one mole of ammonium sulfate? A 1 B 2 C 3 D 4 16 Why is the first ionisation energy of phosphorus greater than the first ionisation energy of silicon? A B C D A phosphorus atom has one more proton in its nucleus. The atomic radius of a phosphorus atom is greater. The outer electron in a phosphorus atom is more shielded. The outer electron in a phosphorus atom is paired. 17 When magnesium nitrate, Mg(NO3)2.7H2O, is heated, which three gases are given off? A B C D dinitrogen oxide, oxygen, water vapour hydrogen, nitrogen, oxygen hydrogen, nitrogen dioxide, oxygen nitrogen dioxide, oxygen, water vapour 18 Sulfur dioxide is used to bleach wood pulp in the production of paper. It is also used as an additive in the production of jam and marmalade, often in the form of sulfite compounds. When it is present in quantities greater than 10 mg / kg it is required to be listed as an ingredient of the jam. Why is sulfur dioxide added to jam? A B C D It is a bleaching agent and removes the undesirable colours from the fruit used in the jam. It is a preservative that destroys unwanted bacteria and enzymes. It is a reducing agent and removes the acids that give the jam a sharp taste. It is an acidic gas and maintains the pH of the jam at a suitable value to give it a sharp taste. © UCLES 2010 9701/13/O/N/10 [Turn over www.XtremePapers.net 6 19 Which property of beryllium and its compounds is typical of the elements below it in Group II? A B C D Be does not react with hot water. BeCl2 is covalent. Be(NO3)2 produces BeO on thermal decomposition. BeO dissolves in alkalis. 20 A compound Y has all of the properties below. • • • It is a liquid at 25 °C. It mixes completely with water. It reacts with aqueous sodium hydroxide. What could Y be? A B C D ethanoic acid ethanol ethene ethyl ethanoate 21 One of the characteristics of addition polymerisation is that the empirical formulae of the polymer and of its monomer are the same. The absorbent material in babies’ disposable nappies is made from the addition polymer shown. CH2 CH CH2 CH CH2 CH CO2H CO2H CO2H From which monomer could this addition polymer be obtained? A B C D CH3CH(OH)CO2H HOCH2CH2CO2H H2C=CHCO2H HO2CCH=CHCO2H © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net 7 22 Compound X reacts with ethanoic acid in the presence of an H+ catalyst to produce the compound below. O H 3C C H C H H C H O O C CH3 What is the molecular formula of compound X? A C2H6O2 B C2H6O3 C C4H8O D C4H8O2 23 Limonene is an oil formed in the peel of citrus fruits. CH3 C CH2 CH3 limonene Which product is formed when an excess of bromine, Br2(l), reacts with limonene at room temperature in the dark? A CH3 C CH2 Br B CH3 C CH2 CH3 C Br C CH2Br CH3 D Br C CH2Br Br CH3 CH3 Br CH3 CH3 Br Br © UCLES 2010 9701/13/O/N/10 [Turn over www.XtremePapers.net 8 24 Tartaric acid is present in some wines. It may be synthesised in the laboratory in two steps. step 1 OHCCHO intermediate step 2 HO2CCH(OH)CH(OH)CO2H tartaric acid Which reagents could be used for this synthesis? step 1 A B C D HCl (aq) HCN, NaCN(aq/alcoholic) H2SO4(aq) KCN(aq/alcoholic) step 2 HCN(g) H2SO4(aq) K2Cr2O7 / H2SO4(aq) K2Cr2O7 / H2SO4(aq) 25 Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)? A B C D butan-1-ol butan-2-ol 2-methylpropan-1-ol 2-methylpropan-2-ol 26 Lactic acid occurs naturally, for example in sour milk. H H H C H O C H lactic acid C O H O What is a property of lactic acid? A B C D It decolourises aqueous bromine rapidly. It is insoluble in water. It reduces Fehling’s reagent. Two molecules react with each other in the presence of a strong acid. © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net 9 27 Which compound would undergo nucleophilic addition? A B C D bromoethane, C2H5Br ethanal, CH3CHO ethane, C2H6 ethene, C2H4 28 Which compound undergoes an SN1 substitution reaction? A B CH3CH2CH2Br (CH3)3CCH2I CH3 Cl C D CH2=CHCl 29 The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic rubber. H C H C CH3 CH3 In addition to 2-methylpropene there are x other isomers of C4H8, structural or otherwise, which contain a double bond. What is the value of x? A 1 B 2 C 3 D 4 30 Which environmental problem is not made worse by the release of oxides of nitrogen from car engines? A B C D acidification of lakes corrosion of buildings photochemical smog the hole in the ozone layer © UCLES 2010 9701/13/O/N/10 [Turn over www.XtremePapers.net 10 Section B For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be correct. Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against the statements that you consider to be correct). The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 31 Which types of intermolecular forces can exist between adjacent urea molecules? O C H 2N urea NH2 1 2 3 hydrogen bonding permanent dipole-dipole forces temporary induced dipole-dipole forces 32 Ethanol is manufactured by reacting ethene gas and steam in the presence of phosphoric(V) acid. C2H4(g) + H2O(g) C2H5OH(g) ∆H = –45 kJ mol–1 The reaction is carried out at 570 K and 60 atm. What would be the consequences of carrying out the reaction at the same temperature but at a pressure of 200 atm? 1 2 3 The manufacturing costs would increase. The maximum yield at equilibrium would be higher. The reaction would proceed at a faster rate. © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net 11 33 The diagram represents the Boltzmann distribution of molecular energies at a given temperature. proportion of molecules energy Which of the factors that affect the rate of a reaction can be explained using such a Boltzmann distribution? 1 2 3 increasing the concentration of reactants increasing the temperature the addition of a catalyst 34 Disproportionation is the term used to describe a reaction in which a reactant is simultaneously both oxidised and reduced. To which incomplete equations does the term disproportionation apply? 1 2 3 Cl2(g) + 2OH–(aq) → H2O(l) + Cl –(aq) + …… 3Cl2(g) + 6OH–(aq) → 3H2O(l) + ClO3–(aq) + …… 2NO2(g) + H2O(l) → HNO3(aq) + …… 35 Samples of calcium and barium are separately added to beakers of cold water containing a few drops of litmus solution. Which observations will be made with only the calcium and not with the barium? 1 2 3 A white suspension appears in the water. The solution turns blue. A gas is evolved. © UCLES 2010 9701/13/O/N/10 [Turn over www.XtremePapers.net 12 The responses A to D should be selected on the basis of A 1, 2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct No other combination of statements is used as a correct response. 36 The diagram shows the structure of the naturally-occurring molecule cholesterol. H 3C CH3 CH3 H H H HO H cholesterol Which statements about cholesterol are correct? 1 2 3 The molecule contains a secondary alcohol group. The molecule contains two π bonds. All carbon atoms in the four rings lie in the same plane. 37 Element X is a solid. It occurs as a contaminant of carbonaceous fuels. Its oxide Y is formed in car engines. Further oxidation of Y to Z can occur in the atmosphere. Which statements about Y and Z are correct? 1 2 3 Molecule Y has lone pairs of electrons. The atmospheric oxidation of Y to Z is a catalysed reaction. Y is a colourless gas. © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net 13 38 An organic compound decolourises aqueous bromine and reacts with sodium to produce hydrogen. Which molecular formula could represent this compound? 1 2 3 C3H6O C3H4O2 C3H8O 39 Textiles for use in aircraft are treated with a finish containing a halogenoalkane. What is the reason for this? 1 2 3 The textile burns less easily, improving safety. The fabric forms hydrogen bonds to water more readily, making the fabric easier to wash. The halogenoalkane undergoes addition polymerisation, stiffening the fabric. 40 Glyceraldehyde, HOCH2CH(OH)CHO, is formed during photosynthesis, and contains a chiral carbon atom. Which reagents will react with glyceraldehyde to produce an organic product without a chiral carbon atom? 1 2 3 warmed acidified K2Cr2O7 NaBH4 Tollens’ reagent © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net 14 BLANK PAGE © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net 15 BLANK PAGE © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net 16 BLANK PAGE Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. University of Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge. © UCLES 2010 9701/13/O/N/10 www.XtremePapers.net