Chapter EightTopic: Nomenclature of Alkenes Section 3 Difficulty: Easy 1. What is the degree of substitution of the following alkene? A. Monosubstituted B. Disubstituted C. Trisubstituted D. Tetrasubstituted Ans: B Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 2. What is the degree of substitution of the following alkene? A. Monosubstituted B. Disubstituted C. Trisubstituted D. Tetrasubstituted Ans: C Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 3. What is the degree of substitution of the following alkene? A. Monosubstituted B. Disubstituted C. Trisubstituted D. Tetrasubstituted Ans: D Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 4. Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. What is the degree of substitution of the alkene of Crestor®? A. Monosubstituted B. Disubstituted C. Trisubstituted D. Tetrasubstituted Ans: B Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 5. Drawn below is the structure of Singulair® (montelukast), a medication used to manage athsma. What is the degree of substitution of the alkene of Singulair®? A. Monosubstituted B. Disubstituted C. Trisubstituted D. Tetrasubstituted Ans: B Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 6. Provide an IUPAC name for the following compound. Ans: 5-methyl-1-hexene Topic: Nomenclature of Alkenes Section 3 Difficulty: Medium 7. Provide an IUPAC name for the following compound. Ans: 3-ethyl-2,4-dimethyl-2-pentene Topic: Nomenclature of Alkenes Section 3 Difficulty: Medium 8. Provide an IUPAC name for the following compound. Ans: 3-methylcyclohexene Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 9. Which of the following is the IUPAC name for the following compound? A. 1-methyl-2-cyclohexene B. 2-methylcyclohexene C. 3-methylcyclohexene D. 1-methyl-5-cyclohexene Ans: C Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 10. Which of the following is the IUPAC name for the following compound? A. 2-ethyl-1,1,3-trimethylbutene B. 3-ethyl-2,4-dimethyl-2-pentene C. 2,4-dimethylhexene D. 4-ethyl-1,3-dimethyl-3-pentene Ans: B Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 11. Which of the following is the correct structure of 4-methylcyclopentene? Ans: B Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 12. Which of the following is the correct structure of 2-methyl-1-butene? Ans: A Topic: Nomenclature of Alkenes Section 3 Difficulty: Medium 13. Draw the structure of 3-methylcyclopentene. Ans: Topic: Nomenclature of Alkenes Section 3 Difficulty: Medium 14. Draw the structure of 2,3-dimethyl-1-pentene. Ans: Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Medium 15. Provide an IUPAC name for the following compound. Ans: E-4-methyl-2-pentene Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Easy 16. Is the geometry of the following alkene E, Z, or neither? Ans: Z Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Easy 17. Is the geometry of the following alkene E, Z, or neither? Ans: E Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Easy 18. Is the geometry of the following alkene E, Z, or neither? Ans: E Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Medium 19. Is the geometry of the following alkene E, Z, or neither? Ans: E Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Medium 20. Draw the E isomer of 2-methyl-3-heptene. Ans: Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Medium 21. Draw the E isomer of 3,4-dimethyl-3-hexene. Ans: Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Easy 22. Draw the Z isomer of 3,4-dimethyl-3-hexene. Ans: Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Hard 23. Viridenomycin, shown below, is a polyene antibiotic that displays anti-tumor activity. Its structural complexity and chemical instability have made it a challenging target for organic chemists to synthesize. Ignoring the benzene ring, how many disubstituted Z alkenes are present in viridenomycin? A. 1 B. 2 C. 3 D. 4 Ans: C Topic: Alkene Stability Section 5 Difficulty: Easy 24. Rank the following from most to least stable. Ans: D, B, A, C Topic: Alkene Stability Section 5 Difficulty: Easy 25. Rank the following from most to least stable. A. A, B, C B. C, B, A C. B, C, A D. B, A, C Ans: C Topic: Alkene Stability Section 5 Difficulty: Medium 26. Which of the following alkenes is more stable? Ans: B Topic: Alkene Stability Section 5 Difficulty: Hard 27. Given the following alkane, draw the least stable alkene isomer with the same basic skeleton. Ans: Topic: Alkene Stability Section 5 Difficulty: Hard 28. Rank the following from most to least stable. Ans: B, C, A Topic: Possible Mechanisms for Elimination Section 6 Difficulty: Medium 29. Show the mechanism for the following elimination, assuming that it is a concerted reaction. Ans: Topic: Possible Mechanisms for Elimination Section 6 Difficulty: Medium 30. Show the mechanism for the following elimination, assuming that it is a concerted reaction. Ans: Topic: Possible Mechanisms for Elimination Section 6 Difficulty: Medium 31. Show the mechanism for the following elimination, assuming that it is a concerted reaction. Ans: Topic: Possible Mechanisms for Elimination Section 6 Difficulty: Easy 32. Which of the following shows a mechanism of a concerted elimination? Ans: A Topic: E2 Mechanism Section 7 Difficulty: Easy 33. Which of the following is the most reactive in an E2 reaction? Ans: C Topic: E2 Mechanism Section 7 Difficulty: Easy 34. Which of the following is the major product of the following elimination? Ans: A Topic: E2 Mechanism Section 7 Difficulty: Easy 35. Which of the following is the major product of the following elimination? Ans: C Topic: E2 Mechanism Section 7 Difficulty: Easy 36. Draw the major product of the following elimination. Ans: Topic: E2 Mechanism Section 7 Difficulty: Medium 37. What would be the best base for performing the following elimination? Ans: KOtBu (or some other hindered strong base) Topic: E2 Mechanism Section 7 Difficulty: Easy 38. Which of the following would be the best base for performing the following elimination? Ans: B or A Topic: E2 Mechanism Section 7 Difficulty: Hard 39. What is the product of the following elimination? Ans: Topic: E2 Mechanism Section 7 Difficulty: Hard 40. What is the product of the following elimination? Ans: Topic: E2 Mechanism Section 7 Difficulty: Hard 41. What is the product of the following elimination? Ans: Topic: E2 Mechanism Section 7 Difficulty: Medium 42. Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide? Ans: B Topic: E2 Mechanism Section 7 Difficulty: Medium 43. Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide? Ans: C or D Topic: E2 Mechanism Section 7 Difficulty: Easy 44. Which of the following alkyl halides would be more reactive in an E2 elimination? Ans: A Topic: E2 Mechanism Section 7 Difficulty: Hard 45. Draw the isomer of 2-bromo-1,1,3-trimethylcyclohexane that would be more reactive in an E2 elimination. Ans: (or enantiomer) Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Medium 46. Draw the major product of the following reaction. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Medium 47. Draw the major product of the following reaction. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Hard 48. Draw the major product of the following reaction. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Hard 49. Draw the major product of the following reaction. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Hard 50. Draw the major product of the following elimination. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Hard 51. Draw the major product of the following reaction. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Medium 52. Draw the major product of the following reaction. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Hard 53. Draw the major product of the following reaction. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Medium 54. Draw the major product of the following reaction. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Easy 55. Draw the major product of the following reaction. Ans: Topic: Drawing the Products of an E2 Reaction Section 8 Difficulty: Easy 56. Draw the major product of the following reaction. Ans: Topic: The E1 Mechanism Section 9 Difficulty: Easy 57. Which of the following is most reactive in an E1 reaction? Ans: C Topic: The E1 Mechanism Section 9 Difficulty: Easy 58. Which of the following is most reactive in an E1 reaction? Ans: C Topic: The E1 Mechanism Section 9 Difficulty: Medium 59. Based upon the following energy diagram, is this reaction an E1 or an E2 elimination? Ans: E2 Topic: The E1 Mechanism Section 9 Difficulty: Medium 60. Based upon the following energy diagram, is this reaction an E1 or an E2 elimination? Ans: E1 Topic: The E1 Mechanism Section 9 Difficulty: Easy 61. For the following dehydration, draw the structure of the intermediate carbocation. Ans: Topic: The E1 Mechanism Section 9 Difficulty: Easy 62. For the following dehydration, draw the structure of the intermediate carbocation. Ans: Topic: The E1 Mechanism Section 9 Difficulty: Easy 63. For the following dehydration, draw the structure of the intermediate carbocation. Ans: Topic: The E1 Mechanism Section 9 Difficulty: Medium 64. Draw the major organic product of the following dehydration reaction. Ans: Topic: The E1 Mechanism Section 9 Difficulty: Medium 65. Draw the product of the following dehydration reaction. Ans: Topic: The E1 Mechanism Section 9 Difficulty: Medium 66. Draw the product of the following dehydration reaction. Ans: Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Hard 67. Draw the mechanism for the following dehydration. Ans: Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Hard 68. Draw the mechanism for the following dehydration. Ans: Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Easy 69. What is the first step of the following dehydration? Ans: C Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Medium 70. Which of the following is the energy diagram for the following reaction? Ans: A Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Medium 71. Draw an energy diagram for the following reaction, assuming that it is exothermic. Ans: Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Easy 72. Which pattern of arrow pushing is associated with the first step in any dehydration reaction? Ans: Proton Transfer Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Hard 73. What are the steps of arrow pushing involved in the following mechanism? Ans: Proton transfer, loss of leaving group, rearrangement, proton transfer Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Easy 74. Will the following alcohol undergo rearrangement during a dehydration reaction? Ans: No Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Easy 75. Will the following alcohol be likely to undergo rearrangement during a dehydration reaction? Ans: Yes Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Hard 76. What is the structure of a rearranged carbocation that does not have a four- membered ring in the following acid-catalyzed dehydration of the following compound? Ans: Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Hard 77. What is the structure of the rearranged carbocation intermediate in the following dehydration? Ans: Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Medium 78. Which of the following is the structure of the rearranged carbocation intermediate in the following dehydration? Ans: B Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Hard 79. Draw the mechanism and product for the following elimination. Ans: Topic: Drawing the Complete E1 Mechanism Section 10 Difficulty: Medium 80. Draw the mechanism and product for the following elimination, without using rearrangement. Ans: Topic: Drawing the Complete E2 Mechanism Section 11 Difficulty: Medium 81. Draw the mechanism and product for the following elimination. Ans: Topic: Drawing the Complete E2 Mechanism Section 11 Difficulty: Medium 82. Draw the mechanism and product for the following elimination. Ans: Topic: Drawing the Complete E2 Mechanism Section 11 Difficulty: Easy 83. Which of the following is the correct mechanism for the elimination reaction of 2- bromo-2,3-dimethylbutane with methoxide? Ans: B Topic: Drawing the Complete E2 Mechanism Section 11 Difficulty: Medium 84. Which of the following is the correct mechanism for the elimination reaction of 1- bromo-2-methylcyclopentane with methoxide? Ans: D Topic: Drawing the Complete E2 Mechanism Section 11 Difficulty: Medium 85. Draw the mechanism and product for the following elimination. Ans: Topic: Drawing the Complete E2 Mechanism Section 11 Difficulty: Medium 86. Draw the mechanism and product for the following elimination. Ans: Topic: Substitution vs Elimination: Identifying the Reagent Section 12 Difficulty: Easy 87. Is the following more likely a nucleophile or a base? Ans: Nucleophile Topic: Substitution vs Elimination: Identifying the Reagent Section 12 Difficulty: Easy 88. Is the following more likely a nucleophile or a base? Ans: Base Topic: Substitution vs Elimination: Identifying the Reagent Section 12 Difficulty: Easy 89. Which of the following is the strongest nucleophile? Ans: C Topic: Substitution vs Elimination: Identifying the Reagent Section 12 Difficulty: Easy 90. Which of the following is the strongest nucleophile? Ans: B Topic: Substitution vs Elimination: Identifying the Reagent Section 12 Difficulty: Easy 91. Which of the following is most likely to act as a base rather than a nucleophile? Ans: C Topic: Substitution vs Elimination: Identifying the Reagent Section 12 Difficulty: Easy 92. Which of the following is most likely to act as a base rather than a nucleophile? Ans: C Topic: Substitution vs Elimination: Identifying the Mechanism Section 13 Difficulty: Easy 93. By what mechanism is the following reaction likely to occur? Ans: SN2 Topic: Substitution vs Elimination: Identifying the Mechanism Section 13 Difficulty: Easy 94. By what mechanism is the following reaction likely to occur? Ans: E2 Topic: Substitution vs Elimination: Identifying the Mechanism Section 13 Difficulty: Easy 95. By what mechanism is the following reaction likely to occur? Ans: SN2 (major) or E2 (minor) Topic: Substitution vs Elimination: Identifying the Mechanism Section 13 Difficulty: Easy 96. By what mechanism is the following reaction likely to occur? Ans: E1 or SN1 Topic: Substitution vs Elimination: Identifying the Mechanism Section 13 Difficulty: Easy 97. By what mechanism is the following reaction likely to occur? Ans: E2 Topic: Substitution vs Elimination: Identifying the Mechanism Section 13 Difficulty: Easy 98. How would you change the following reaction conditions to favor an E2 mechanism? Ans: Use a stronger base Topic: Substitution vs Elimination: Identifying the Mechanism Section 13 Difficulty: Easy 99. How would you change the following reaction conditions to favor an E1 mechanism? Ans: Use a weaker base Topic: Substitution vs Elimination: Predicting the Products Section 14 Difficulty: Medium 100. What is (are) the most likely product(s) for the following reaction? Ans: Topic: Substitution vs Elimination: Predicting the Products Section 14 Difficulty: Medium 101. What is (are) the most likely product(s) for the following reaction? Ans: Topic: Substitution vs Elimination: Predicting the Products Section 14 Difficulty: Hard 102. What is (are) the most likely product(s) for the following reaction? Ans: Topic: Substitution vs Elimination: Predicting the Products Section 14 Difficulty: Hard 103. What is (are) the most likely product(s) for the following reaction? Ans: Topic: Substitution vs Elimination: Predicting the Products Section 14 Difficulty: Medium 104. What is (are) the most likely product(s) for the following reaction? Ans: Topic: Substitution vs Elimination: Predicting the Products Section 14 Difficulty: Medium 105. What is (are) the most likely product(s) for the following reaction? Ans: Topic: Substitution vs Elimination: Predicting the Products Section 14 Difficulty: Hard 106. What is (are) the most likely product(s) for the following reaction? Ans: Topic: Substitution vs Elimination: Predicting the Products Section 14 Difficulty: Hard 107. What is (are) the most likely product(s) for the following reaction? Ans: Topic: Integrated Section 3 + 4 Difficulty: Medium 108. Viridenomycin, shown below, is a polyene antibiotic that displays anti- tumor activity. Its structural complexity and chemical instability have made it a challenging target for organic chemists to synthesize. Ignoring the benzene ring, circle any trisubstituted alkene(s), and put a box around any Z alkene(s). Ans: Topic: Stereoisomerism in Alkenes + Spectroscopy Section 4 + Spectroscopy Difficulty: Medium 109. How many distinct signals would appear in the (proton-decoupled) 13C NMR spectrum for the following compound? A. 4 B. 5 C. 6 D. 8 Ans: A Topic: Stereoisomerism in Alkenes + Spectroscopy Section 4 + Spectroscopy Difficulty: Medium 110. How many distinct resonances would appear in the (proton-decoupled) 13C NMR spectrum in the region between 100-130 ppm for the following compound? A. 3 B. 4 C. 5 D. 6 Ans: B Topic: Stereoisomerism in Alkenes + Spectroscopy Section 4 + Spectroscopy Difficulty: Medium 111. A student runs an elimination reaction in lab, beginning with 1-iodo-1- methyl cyclohexane. If the product obtained shows exactly 5 distinct carbons in the (proton-decoupled) 13C NMR spectrum, what base could have been used to cause the elimination? Ans: tert-butoxide