CHAPTER 6—REACTIONS OF ALKENES

MULTIPLE CHOICE

1. What type of carbocation is shown?

a. primary
b. secondary
c. tertiary
d. quaternary
ANS: B

2. What type of carbocation is shown?

a. primary
b. secondary
c. tertiary
d. quaternary
ANS: C

3. Which of the following concepts explains why tertiary carbocations are more stable than primary and
secondary carbocations?
a. electronegativity
b. resonance
c. hyperconjugation
d. the octet rule
ANS: C

4. What type of orbitals overlap to provide stability to the tert-butyl carbocation by hyperconjugation?
a. 3° C 2p atomic orbital + 3° C sp2 atomic orbital
b. 3° C 2p atomic orbital + methyl C−H σ molecular orbital
c. 3° C sp2 atomic orbital + methyl C−H σ molecular orbital
d. 3° C 2p atomic orbital + methyl C 2s atomic orbital
ANS: B

5. Which of the following concepts explains Markovnikov's rule as applied to the addition of HBr to
propene?
a. the relative stability of carbocations
b. the nucleophilicity of bromide anion
c. the acidity of HBr
d. the Aufbau principle

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 ANS: A

6. What is the correct order of stability of the following carbocations (more stable > less stable)?

a. 1>2>3
b. 1>3>2
c. 3>1>2
d. 3>2>1
ANS: D

7. What is the correct order of stability of the following carbocations (more stable > less stable)?

a. 1>2>3
b. 2>1>3
c. 2>3>1
d. 3>2>1
ANS: C

8. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: B

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 9. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: B

10. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: C

11. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: C

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 12. Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration
(treatment with aqueous H2SO4)?

a. 1
b. 2
c. 3
d. 4
ANS: B

13. Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration
(treatment with aqueous H2SO4)?

a. 1
b. 2
c. 3
d. 4
ANS: B

14. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: C

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 15. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: C

16. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: B

17. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: B

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 18. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: B

19. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: C

20. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: B

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 21. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: B

22. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: C

23. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: B

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 24. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: C

25. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: D

26. What is the major product obtained upon addition of Br2 to (R)-4-tert-butylcyclohexene?
a. (1R,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane
b. (1S,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane
c. (1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane
d. (1S,2S,4S)-1,2-dibromo-4-tert-butylcyclohexane
ANS: C

27. What is (are) the major organic product(s) obtained from the following reaction?

1. (2R,3R)-dibromobutane
2. (2S,3S)-dibromobutane
3. meso-2,3-dibromobutane

a. only 1
b. only 2
c. only 3
d. only 1 and 2

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 ANS: C

28. What is (are) the major organic product(s) obtained from the following reaction?

1. (2R,3R)-dibromobutane
2. (2S,3S)-dibromobutane
3. meso-2,3-dibromobutane

a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: D

29. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: B

30. What is the major organic product obtained from the following reaction?

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 a. 1
b. 2
c. 3
d. 4
ANS: A

31. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4
ANS: D

32. What is (are) the major organic product(s) obtained from the following reaction?

1. (2R,3R)-butanediol
2. (2S,3S)-butanediol
3. meso-2,3-butanediol

a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: D

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 33. What is (are) the major organic product(s) obtained from the following reaction?

1. (2R,3R)-butanediol
2. (2S,3S)-butanediol
3. meso-2,3-butanediol

a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: C

34. What is (are) the major organic product(s) obtained from the following reaction?

a. only 1
b. only 2
c. only 3
d. only 2 and 3
ANS: A

35. What is the best choice of reagent(s) to perform the following transformation?

a. H2O, H2SO4
b. HgSO4; followed by NaBH4
c. BH3; followed by H2O2
d. OsO4; followed by NaHSO3
ANS: D

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 36. What is the best choice of reagent to perform the following transformation?

a. Br2
b. HBr
c. Br2, H2O
d. N-bromosuccinimide
ANS: C

37. What is the best choice of reagent(s) to perform the following transformation?

a. H2O, H2SO4
b. Hg(OAc)2 and H2O ; followed by NaBH4
c. B2H6; followed by H2O2, NaOH
d. OsO4; followed by NaHSO3
ANS: C

38. What is the best choice of reagent(s) to perform the following transformation?

a. O3; followed by (CH3)2S

b. Hg(OAc)2 and H2O; followed by NaBH4
c. BH3; followed by H2O2, NaOH
d. OsO4; followed by NaHSO3
ANS: A

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 39. What is the best choice of reagent(s) to perform the following transformation?

a. H2O, H2SO4
b. Hg(OAc)2 and H2O; followed by NaBH4
c. BH3; followed by H2O2, NaOH
d. OsO4; followed by NaHSO3
ANS: B

40. What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a
bromoalkane?
a. carbocation
b. carbanion
c. radical
d. cyclic bromonium ion
ANS: A

41. What type of reactive intermediate is formed in the reaction of an alkene with Br2 and water to give a
bromohydrin?
a. carbocation
b. carbanion
c. radical
d. cyclic bromonium ion
ANS: D

42. What type of reactive intermediate is formed in the reaction of an alkene with aqueous acid to give an
alcohol?
a. carbocation
b. carbanion
c. radical
d. carbene
ANS: A

43. What type of reaction mechanism accounts for the reaction of an alkene with aqueous acid to give an
alcohol?
a. nucleophilic addition
b. electrophilic addition
c. radical addition
d. elimination
ANS: B

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 44. What type of reaction mechanism accounts for the reaction of an alkene with HBr to give an alkyl
bromide?
a. nucleophilic addition
b. electrophilic addition
c. radical addition
d. elimination
ANS: B

45. Which of the following alkenes undergoes the most exothermic hydrogenation upon treatment with
H2/Pd?

a. 1
b. 2
c. 3
d. 4
ANS: D

46. Which of the following alkenes undergoes the least exothermic hydrogenation upon treatment with
H2/Pd?

a. 1
b. 2
c. 3
d. 4
ANS: C

47. What is the correct order of exothermicity for hydrogenation of the following butenes upon treatment
with H2/Pd (more exothermic > less exothermic)?

a. 1>2>3
b. 1>3>2
c. 3>2>1
d. 2>3>1
ANS: A

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 48. What is (are) the major organic product(s) obtained from the following reaction?

1. (R)-2-bromo-3-methylbutane
2. (S)-2-bromo-3-methylbutane
3. 2-bromo-2-methylbutane

a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: C

49. What is (are) the major organic product(s) obtained from the following reaction?

1. (R)-3-methyl-2-butanol
2. (S)-3-methyl-2-butanol
3. 2-methyl-2-butanol

a. only 1
b. only 2
c. only 3
d. only 1 and 2
ANS: D

50. Which of the following reactions of alkenes is not stereospecific?

a. bromination (treatment with Br2 in CHCl3)
b. hydrogenation (treatment with H2/Pt)
c. acid-catalyzed hydration (treatment with aqueous H2SO4)
d. bromohydrin formation (treatment with Br2/H2O)
ANS: C

51. Which of the following reactions of alkenes is stereospecific?

a. addition of HCl (treatment with HCl)
b. hydrogenation (treatment with H2/Pt)
c. addition of HBr (treatment with HBr)
d. acid-catalyzed hydration (treatment with aqueous H2SO4)
ANS: B

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 52. Which of the following reactions of alkenes takes place with anti stereospecificity?
a. bishydroxylation (treatment with OsO4 followed by NaHSO3)
b. hydrogenation (treatment with H2/Pt)
c. addition of HBr (treatment with HBr)
d. bromohydrin formation (treatment with Br2, H2O)
ANS: D

53. Which of the following reactions of alkenes takes place with syn stereospecificity?
a. addition of bromine (treatment with Br2)
b. hydrogenation (treatment with H2/Pt)
c. addition of HBr (treatment with HBr)
d. acid-catalyzed hydration (treatment with aqueous H2SO4)
ANS: B

PROBLEM

1. What is the major organic product obtained from the following reaction?

ANS:

2. What is the major organic product obtained from the following reaction?

ANS:

3. What is the major organic product obtained from the following reaction?

ANS:

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 4. What is the major organic product obtained from the following reaction?

ANS:

5. What is the major organic product obtained from the following reaction?

ANS:

6. What is the major organic product obtained from the following reaction?

ANS:

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 7. What is the major organic product obtained from the following reaction?

ANS:

8. What is the major organic product obtained from the following reaction?

ANS:

9. What is the major organic product obtained from the following reaction?

ANS:
2 equivalents of

10. What is the major organic product obtained from the following reaction?

ANS:

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 11. What is the major organic product obtained from the following reaction?

ANS:

12. What is the best choice of reagent(s) to perform the following transformation?

ANS:
(i) BH3; (ii) H2O2, NaOH

13. What is the best choice of reagent(s) to perform the following transformation?

ANS:
H2O, H2SO4
or
(i) Hg(OAc)2, H2O; (ii) NaBH4

14. What is the best choice of reagent(s) to perform the following transformation?

ANS:
(i) OsO4; (ii) NaHSO3, H2O

15. What is the best choice of reagent(s) to perform the following transformation?

ANS:
H2, transition metal catalyst (e.g., Pt, Pd)

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 16. What is the best choice of reagent(s) to perform the following transformation?

ANS:
Br2

17. What is the best choice of reagent(s) to perform the following transformation?

ANS:
Br2, H2O

18. What is the best choice of reagent(s) to perform the following transformation?

ANS:
HBr

19. What is the best choice of reagent(s) to perform the following transformation?

ANS:
(i) O3 (ii) (CH3)2S

20. Provide the structure of the key intermediate in the following reaction?

ANS:

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 21. Provide the structure of the key intermediate in the following reaction?

ANS:

22. Provide the structure of the key intermediate in the following reaction?

ANS:

23. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the
movement of paris of electrons and the structure of reactive intermediates.

ANS:
The reaction proceeds in two steps:
1. Protonation of propene to form the 2-propyl cation
2. Nucleophilic addition of bromide anion to the 2-propyl cation

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 24. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the
movement of paris of electrons and the structure of reactive intermediates.

ANS:
The reaction proceeds in three steps:
1. Protonation of propene to form the 2-propyl cation
2. Nucleophilic addition of bromine to the 2-propyl cation
3. Deprotonation of the oxygen

25. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the
movement of paris of electrons and the structure of reactive intermediates.

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 ANS:
The reaction proceeds in two steps:
1. Addition of bromine to propene to afford a cyclic bromonium ion
2. Nucleophilic ring-opening addition of bromide anion

26. Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the
movement of paris of electrons and the structure of reactive intermediates.

ANS:
The reaction proceeds in three steps:
1. Addition of bromine to propene to afford a cyclic bromonium ion
2. Nucleophilic ring-opening addition of water
3. Deprotonation of oxygen

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