CHAPTER 17—CARBOXYLIC ACIDSMULTIPLE CHOICE 1. What is the IUPAC name of the following compound a. b. c. d. 3,3-dimethylhexanoic acid 2,2-dimethylpentanoic acid 2,2-dimethylpentanal 4,4-dimethyl-6-hexanoyl acid ANS: A 2. What is the IUPAC name of the following compound? a. b. c. d. 5,5-dimethyl-5-phenylpentanoic acid 5-methyl-5-phenylhexanoic acid 2,2-dimethylphenylpropanoic acid 5,5-dimethyl-5-phenylbutanal ANS: B 3. What is the IUPAC name of the following compound? a. b. c. d. (E)-4-ethyl-3-pentenoic acid (Z)-4-ethyl-3-pentenoic acid (E)-4-methyl-3-hexenoic acid (Z)-4-methyl-3-hexenoic acid ANS: D Brown Organic Chemistry 6e Test Bank 1 4.3R)-dihydroxybutanedioic acid ANS: B 6. d. b. cis-4-methylcyclohexanecarboxylic acid trans-4-methylcyclohexanecarboxylic acid cis-3-methylcyclohexanecarboxylic acid trans-3-methylcyclohexanecarboxylic acid ANS: A Brown Organic Chemistry 6e Test Bank 2 . c. c. What is the IUPAC name of the following compound? a.3S)-dihydroxybutanedioic acid (2R. What is the IUPAC name of the following compound? a. c. (2R. d.4-dimethyl-3-phenyl-3-butenoic acid 3-phenyl-2-methyl-2-penten-5-oic acid (Z)-3-methyl-2-phenyl-2-butenoic acid ANS: A 5. What is the IUPAC name of the following compound? a.3R)-dihydroxybutanedioic acid (2S. b.3S)-dihydroxybutanedioic acid (2S. d. 4-methyl-3-phenyl-3-pentenoic acid 4. b. b. 4 = adipic acid 1 = oxalic acid. 3 = succinic acid. 2 = benzoic acid. butanoic acid ANS: D 10. d. 4 = oxalic acid ANS: B 9. c. butanoic acid d. 2 = succinic acid. 1 = salicylic acid. What is the correct assignment of the names of the following substituted benzenes? a. 3 = terephthalic acid. 4 = benzoic acid 1 = phthalic acid. 2 = terephthalic acid. acetic acid b. pentanal ANS: A Brown Organic Chemistry 6e Test Bank 3 . 2 = salicylic acid. 3 = malonic acid. 3 = succinic acid. 3 = adipic acid. 2 = oxalic acid. 4 = phthalic acid 1 = salicylic acid. b. 3 = terephthalic acid. 2 = malonic acid. 2 = malonic acid. pentanol c. Which of the following is the most soluble in water? a. Which of the following is the most soluble in water? a. 4 = malonic acid 1 = adipic acid. 3 = phthalic acid. 2 = benzoic acid. 1-pentanol c. 3 = benzoic acid.7. hexane b. d. 4 = adipic acid 1 = oxalic acid. c. 4 = phthalic acid 1 = terephthalic acid. What is the correct assignment of the names of the following substituted benzenes? a. 4 = salicylic acid ANS: A 8. 1 = succinic acid. pentanal d. Cl2CHCOOH > ClCH2COOH > CH3COOH c. What is the approximate pKa value of acetic acid a. CH3CH2OH > FCH2COOH > ClCH2COOH ANS: A Brown Organic Chemistry 6e Test Bank 4 . 2 b. hexane b. CH3COOH > ClCH2COOH > Cl2CHCOOH c. Benzoic acid is extracted out of diethyl ether by treatment with aqueous sodium bicarbonate. CH3COOH > ClCH2COOH > CH3OH ANS: B 16.11. ANS: C 15. ICH2COOH > ClCH2COOH > FCH2COOH b. FCH2COOH > CH3COOH > F2CHCOOH b. acetic acid b. 15 d. 5 c. Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)? a. Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)? a. CH3CH2OH > FCH2COOH > ClCH2COOH d. Which of the following has the highest boiling point? a. Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)? a. CH3COOH > FCH2COOH > CH3CH2OH d. butanoic acid d. pentanal ANS: C 13. pentanol c. b. Which of the following statements is not true regarding benzoic acid acids? a. Which of the following has the highest boiling point? a. pentanal d. The neutral acid is the predominant species in aqueous solution at pH <2. 35 ANS: B 14. The anionic carboxylate is the predominant species in aqueous solution at pH >7. CH3CH2OH > ClCH2COOH > BrCH2COOH d. butanoic acid ANS: D 12. FCH2COOH > ClCH2COOH > BrCH2COOH b. c. CH3COOH > FCH2COOH > CH3CH2OH ANS: B 17. d. Sodium benzoate is less soluble in water than benzoic acid. 1-pentanol c. FCH2COOH > CH3COOH > CH3OH c. What is the major organic product obtained from the following reaction? a. b. b. d. c.18. d. What is the major organic product obtained from the following reaction? a. c. 1 2 3 4 ANS: C Brown Organic Chemistry 6e Test Bank 5 . 1 2 3 4 ANS: B 19. 1 2 3 4 ANS: B 21. b.20. d. d. c. What is the major organic product obtained from the following reaction? a. b. 1 2 3 4 ANS: C Brown Organic Chemistry 6e Test Bank 6 . c. What is the major organic product obtained from the following reaction? a. d. b. c. 1 2 3 4 ANS: A 23.22. What is the major organic product obtained from the following reaction? a. c. What is the major organic product obtained from the following reaction? a. d. b. 1 2 3 4 ANS: A Brown Organic Chemistry 6e Test Bank 7 . b. What is the major organic product obtained from the following reaction? a. b. d. 1 2 3 4 ANS: B 25.24. 1 2 3 4 ANS: B Brown Organic Chemistry 6e Test Bank 8 . c. What is the major organic product obtained from the following reaction? a. c. d. b. d. 1 2 3 4 ANS: A Brown Organic Chemistry 6e Test Bank 9 .26. c. c. What is the major organic product obtained from the following reaction? a. b. What is the major organic product obtained from the following reaction? a. d. 1 2 3 4 ANS: C 27. 28. What is the major organic product obtained from the following reaction? a. b. What is the major organic product obtained from the following reaction? a. 1 2 3 4 ANS: A Brown Organic Chemistry 6e Test Bank 10 . b. c. d. d. c. 1 2 3 4 ANS: C 29. b. What is the major organic product obtained from the following reaction? a.30. What is the major organic product obtained from the following reaction? a. d. b. 1 2 3 4 ANS: D 31. 1 2 3 4 ANS: D Brown Organic Chemistry 6e Test Bank 11 . c. c. d. b. 1 2 3 4 ANS: C Brown Organic Chemistry 6e Test Bank 12 . Which of the following carboxylic acids undergoes the most rapid thermal decarboxylation reaction? a. d. What is the major organic product obtained from the following reaction? a. c. d. c.32. 1 2 3 4 ANS: C 33. b. c. d. 2. NaBH4. 1. 2. Pt 1. What is the best choice of reagent(s) to perform the following transformation? a. LiAlH4. 2. What is the best choice of reagent(s) to perform the following transformation? a. What is the best choice of reagent(s) to perform the following transformation? a. 2. CH3I. c. H2SO4 NaOCH3 CH3Li ANS: A 35. c. LiAlH4. b. H2SO4 CH3MgBr LiOCH3 CH2N2 ANS: D 36. d. c.34. CH3OH. b. H2SO4 CH3I. b. d. H3O+ H2. H2O NaH ANS: B Brown Organic Chemistry 6e Test Bank 13 . Pt 1. d. b. 1. H3O+ H2. H2O NaH ANS: A 37. NaBH4. What is the best choice of reagent(s) to perform the following transformation? a. c. b. Pt 1. substitution followed by addition c. What is the best choice of reagent to perform the following transformation? a. carbanion d. 2. addition followed by elimination b. Which of the following is a reactive intermediate in the thermal decarboxylation of a 1. carboxylate ANS: A 41. b.3-diacid? a. H3O+ H2. H2O NaH ANS: C 39. carbocation c. Which of the following best describes the key mechanistic steps in the esterification of a carboxylic acid upon treatment with an alcohol in the presence of a strong acid? a. enol b. What is the best choice of reagent(s) to perform the following transformation? a. d. NaBH4. d.38. LiAlH4. NaCl HCl SOCl2 Cl2 ANS: C 40. c. 2. 1. elimination followed by addition d. addition followed by decarboxylation ANS: A Brown Organic Chemistry 6e Test Bank 14 . What is the major organic product obtained from the following reaction? ANS: 4. What is the IUPAC name of the following compound? ANS: (E)-3-pentenoic acid 3.PROBLEM 1. What is the IUPAC name of the following compound? ANS: (Z)-2-butenoic acid 2. What is the major organic product obtained from the following reaction? ANS: Brown Organic Chemistry 6e Test Bank 15 . What is the major organic product obtained from the following reaction? ANS: 7. What is the major organic product obtained from the following reaction? Brown Organic Chemistry 6e Test Bank 16 . What is the major organic product obtained from the following reaction? ANS: 6.5. What is the major organic product obtained from the following reaction? ANS: 10.ANS: 8. What is the major organic product obtained from the following reaction? ANS: Brown Organic Chemistry 6e Test Bank 17 . What is the major organic product obtained from the following reaction? ANS: 9. 11. What is the major organic product obtained from the following sequence of reactions? ANS: 12. What is the major organic product obtained from the following sequence of reactions? ANS: Brown Organic Chemistry 6e Test Bank 18 .