Chapter 8: Alkyl Halides and Elimination Reactions
1. Which of the following statements about an E1 mechanism is not true?
A) It is a two-step process and has the same first step as an SN1 mechanism.
B) It involves the formation of a carbocation from eliminating a good leaving group.
C) A common competing reaction is rearrangement of a less stable carbocation to a
more stable carbocation.
D) The loss of a proton by the carbocation is a slow step.
2. How many unique β carbons are found in the alkyl halide below?
A) 1
B) 2
C) 3
D) 4
3. How many unique β carbons are found in the alkyl halide below?
A) 1
B) 2
C) 3
D) 4
4. Classify each alkene in vitamin D3 labeled I, II, III by the number of carbon substituents
bonded to the double bond.
A)
B)
C)
D)
I = Disubstituted; II = trisubstituted; III = trisubstituted.
I = Monosubstituted; II = disubstituted; III = trisubstituted.
I = Disubstituted; II = disubstituted; III = trisubstituted.
I = Disubstituted; II = trisubstituted; III = disubstituted.
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Chapter 8: Alkyl Halides and Elimination Reactions
5. Which of the following represents the rate law for an E2 reaction?
A) Rate = k[alkyl halide]
C) Rate = k[alkyl halide]2
B) Rate = k[alkyl halide][base]
D) Rate = k[base]2
6. Which of the following statements about the mechanism of an E2 reaction is true?
A) All bonds are broken and formed in multiple steps.
B) The reaction is not concerted.
C) Entropy favors the reactants of an E2 reaction.
D) Entropy favors the products of an E2 reaction.
7. How many different E2 products can form from the dehydrohalogenation of
2-bromobutane?
A) 1
B) 2
C) 3
D) 4
8. What is the major elimination product in the reaction of 1-bromobutane with potassium
tert-butoxide in tert-butanol?
A) cis-2-Butene
B) 1-Butene
C) trans-2-Butene
D) Butanol
9. What is the major product of the following reaction?
A) I
B) II
C) III
D) IV
10. Which of the following statements about the mechanism of an E2 reaction is not true?
A) It is fastest with tertiary halides.
B) It exhibits first-order kinetics.
C) A better leaving group should make a faster reaction.
D) All bonds are broken and formed in a single step.
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Chapter 8: Alkyl Halides and Elimination Reactions
11. What is the major elimination product obtained from the following reaction?
A) I
B) II
C) III
D) IV
12. What is the major elimination product obtained from the following reaction?
A) I
B) II
C) III
D) IV
13. What is the major elimination product obtained from the following reaction?
A) I
B) II
C) III
D) IV
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Chapter 8: Alkyl Halides and Elimination Reactions
14. What is the major elimination product obtained from the following reaction?
A) I
B) II
C) III
D) IV
15. Which of the following is the most reactive substrate in an E2 reaction?
A) I
B) II
C) III
D) IV
16. Which of the following is the least reactive substrate in an E2 reaction?
A) I
B) II
C) III
D) IV
17. Which of the following statements about an E1 mechanism is not true?
A) The reaction is fastest with tertiary alkyl halides.
B) A better leaving group makes the reaction rate increase.
C) The reaction follows first-order kinetics.
D) Stronger bases favor the E1 reaction.
18. Which of the following statements about an E1 mechanism is true?
A) The identity of the leaving group affects the rate of reaction.
B) The reaction follows second-order kinetics.
C) The reaction is slowest with tertiary substrates.
D) Polar aprotic solvents favor the E1 mechanism.
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Chapter 8: Alkyl Halides and Elimination Reactions
19. Which of the following is the most reactive substrate in an E1 reaction?
A) I
B) II
C) III
D) IV
20. Which of the following is the major elimination product of the following reaction?
A) I
B) II
C) III
D) IV
21. Which of the following alkyl halides would afford the indicated product upon reaction
with sodium methoxide?
A) I
B) II
C) III
D) IV
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Chapter 8: Alkyl Halides and Elimination Reactions
22. Which of the following is the major E2 product formed from the following alkyl halide?
A) I
B) II
C) III
D) IV
23. Which of the labeled protons in the compound below is most readily abstracted under
E2 conditions?
A) Ha
B) Hb
C) Hc
D) Hd
24. Which of the following alkyl halides will afford the product below as the major product
in an E2 reaction?
A) I
B) II
C) III
D) IV
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Chapter 8: Alkyl Halides and Elimination Reactions
25. What is the product of the following reaction?
A) I
B) II
C) III
D) IV
26. What is the product of the following reaction?
A) I
B) II
C) III
D) IV
27. What is the product of the following reaction?
A) I
B) II
C) III
D) IV
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Chapter 8: Alkyl Halides and Elimination Reactions
28. What is the product of the following reaction?
A) Only I
B) Only II
C) Only III
D) II and III
29. Which of the following is most likely to react as a base rather than a nucleophile?
A) I
B) II
C) III
D) IV
30. Which of the following is most likely to react as a nucleophile rather than a base?
A) I
B) II
C) III
D) IV
31. Which of the following is the dihalide that can be used to prepare the alkyne below?
A) Only I
B) Only II
C) Only III
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D) II and III
Chapter 8: Alkyl Halides and Elimination Reactions
32. Which of the following is the dihalide that can be used to prepare the alkyne below?
A) I and II
B) II and III
C) I and III
D) I, II and III
33. Select the elimination product(s) formed by treating the indicated alkyl halide with a
base.
A) Only I
B) Only II
C) Only III
D) I, II and III
34. What is (are) the product(s) of the following reaction?
A) I and II
B) II and III
C) I and III
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D) I, II and III
Chapter 8: Alkyl Halides and Elimination Reactions
35. What is (are) the product(s) of the following reaction?
A) Only I
B) Only II
C) Only III
D) II and III
36. What is (are) the elimination product(s) of the following reaction?
A) Only I
B) Only II
C) Only III
D) II and III
37. What is (are) the elimination product(s) of the following reaction?
A) Only I
B) Only II
C) Only III
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D) II and III
Chapter 8: Alkyl Halides and Elimination Reactions
38. What is (are) the product(s) of the following reaction?
A) Only I
B) Only II
C) Only III
D) I and II
39. What is (are) the product(s) of the following reaction?
A) Only I
B) Only II
C) Only III
D) I and II
40. What is (are) the starting material(s) in the reaction below?
A) Only I
B) Only II
C) Only III
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D) II and III
Chapter 8: Alkyl Halides and Elimination Reactions
41. Which alkyl halide(s) would give the following alkene as the only product in an
elimination reaction?
A) Only I
B) Only II
C) Only III
D) I and II
42. What is the most likely mechanism for the reaction below?
A) SN1
B) SN2
C) E1
D) E2
43. What is the most likely mechanism for the reaction below?
A) SN1
B) SN2
C) E1
D) E2
44. Consider the following E2 reaction. What rate equation would be observed for this
reaction?
A)
B)
C)
D)
Rate = k[CH3CH2CH2Br]
Rate = k[CH3CH2CH2Br][KOC(CH3)3]
Rate = k[CH3CH2CH2Br][KOC(CH3)3]2
Rate = k[CH3CH2CH2Br]2[KOC(CH3)3]
45. Which of the following alkenes is the most stable?
A) I
B) II
C) III
D) IV
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Chapter 8: Alkyl Halides and Elimination Reactions
Answer Key
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.
43.
44.
D
B
B
A
B
D
C
B
D
B
A
A
B
A
D
A
D
A
B
D
D
B
D
D
D
B
D
D
D
B
D
D
D
D
D
D
D
A
B
A
B
B
D
B
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Chapter 8: Alkyl Halides and Elimination Reactions
45. A
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