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Chapter Eight

Topic: 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