Chapter Eight
Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 1. What is the degree of substitution of the following alkene?
A. B. C. D.
Monosubstituted Disubstituted Trisubstituted Tetrasubstituted
Ans: B Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 2. What is the degree of substitution of the following alkene?
A. B. C. D.
Monosubstituted Disubstituted Trisubstituted 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 to reduce cholesterol. What is the degree of substitution substitution of the alkene of Crestor®? 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), (montelukast), a medication used to to manage athsma. What is the degree of substitution substitution of the alkene of Singulair®? 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 following compound. Ans: 5-methyl-1-hexene Topic: Nomenclature of Alkenes Section 3 Difficulty: Medium
7. Provide an IUPAC name for the following 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 following compound.
Ans: 3-methylcyclohexene Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 9. Which of the following is the IUPAC 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:
-4-methyl-2-pentene E -4-methyl-2-pentene
Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Easy 16. Is the geometry of the following alkene alken e E , Z , or neither?
Ans:
Z
Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Easy 17. Is the geometry of the following alkene alken e E , Z , or neither? Ans:
E
Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Easy 18. Is the geometry of the following alkene alken e E , Z , or neither?
Ans:
E
Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Medium 19. Is the geometry of the following alkene alken e E , Z , or neither?
Ans:
E
Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Medium 20. Draw the E isomer isomer of 2-methyl-3-heptene. Ans: Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Medium 21. Draw the E isomer isomer of 3,4-dimethyl-3-hexene. Ans: Topic: Stereoisomerism in Alkenes Section 4 Difficulty: Easy
22. Draw the Z isomer 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 structural complexity and chemical instability have made it a challenging target for organic chemists to synthesize. Ignoring the benzene ring, 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 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 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 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 Mechanisms for Elimination Section 6 Difficulty: Easy 32. Which of the following shows a mechanism mecha nism 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 p roduct of the following elimination?
Ans: A Topic: E2 Mechanism Section 7 Difficulty: Easy 35. Which of the following is the major product p roduct 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 a fford 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 a fford 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 b e 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 energ y 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 energ y 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 the Complete E1 Mechanism Section 10 Difficulty: Hard 67. Draw the mechanism for the following deh ydration.
Ans:
Topic: Drawing the the Complete E1 Mechanism Section 10 Difficulty: Hard 68. Draw the mechanism for the following deh ydration.
Ans:
Topic: Drawing the the Complete E1 Mechanism Section 10 Difficulty: Easy 69. What is the first step of the following deh ydration?
Ans: C Topic: Drawing the the Complete E1 Mechanism Section 10 Difficulty: Medium 70. Which of the following is the energy energ y diagram for the following reaction?
Ans: A Topic: Drawing the 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 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 the Complete E1 Mechanism Section 10 Difficulty: Hard 73. What are the steps of arrow pushing invo lved in the following mechanism?
Ans: Proton transfer, loss of leaving leaving group, rearrangement, proton proton transfer Topic: Drawing the the Complete E1 Mechanism Section 10 Difficulty: Easy 74. Will the following alcohol undergo rearrangement during a dehydration reaction?
Ans: No Topic: Drawing the the Complete E1 Mechanism Mechanism Section 10 Difficulty: Easy 75. Will the following alcohol be likely to undergo rearrangement during a dehydration reaction?
Ans: Yes Topic: Drawing the the Complete E1 Mechanism Section 10 Difficulty: Hard 76. What is the structure of a rearranged ca rbocation that does not have a fourmembered ring in the following acid-catalyzed dehydration of the following compound?
Ans: Topic: Drawing the 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 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 the Complete E1 Mechanism Section 10 Difficulty: Hard 79. Draw the mechanism and product for the following elimination.
Ans:
Topic: Drawing the 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 the Complete E2 Mechanism Section 11 Difficulty: Medium 81. Draw the mechanism and product for the following elimination.
Ans:
Topic: Drawing the the Complete E2 Mechanism Section 11 Difficulty: Medium 82. Draw the mechanism and product for the following elimination.
Ans:
Topic: Drawing the 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 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 the Complete E2 Mechanism Section 11 Difficulty: Medium 85. Draw the mechanism and product for the following elimination.
Ans:
Topic: Drawing the the Complete E2 Mechanism Section 11 Difficulty: Medium 86. Draw the mechanism and product for the following elimination.
Ans:
Topic: Substitution vs Elimination: 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: 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: Elimination: Identifying the Reagent Section 12 Difficulty: Easy 89. Which of the following is the strongest nucleophile?
Ans: C Topic: Substitution vs Elimination: Elimination: Identifying the Reagent Section 12 Difficulty: Easy 90. Which of the following is the strongest nucleophile?
Ans: B Topic: Substitution vs Elimination: 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? nu cleophile?
Ans: C Topic: Substitution vs Elimination: 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? nu cleophile?
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: S N2 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: S N2 (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 S N1 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 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: 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: 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: 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: 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: 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: 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: 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: 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 antitumor activity. Its structural complexity and chemical instability have made it a challenging target for organic chemists to synthesize. Ignoring the benzene ring, ring, circle any trisubstituted alkene(s), and put a box around any Z alkene(s). 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-1methyl cyclohexane. If the product obtained shows exactly 5 distinct carbons carbons in 13 the (proton-decoupled) C NMR spectrum, what base could have been used to cause the elimination? Ans: tert-butoxide
