Chapter Eleven

MULTIPLE CHOICE QUESTIONS

Topic: Structure and Nomenclature

Section: 5.3 and 11.1
Difficulty Level: Hard

1. What is the relationship between alcohols I and II?

CH3
OH

CH3

HO

I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
Ans: C

703
Topic: Structure and Nomenclature
Section: 5.3 and 11.1
Difficulty Level: Hard

2. What is the relationship between alcohols I and II?

CH3 CH3

OH
OH

I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
Ans: C

Topic: Structure and Nomenclature

Section: 5.3 and 11.1
Difficulty Level: Hard

3. What is the relationship between alcohols I and II?

CH3 OH

OH
CH3

I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
Ans: C

704
Topic: Structure and Nomenclature
Section: 5.3 and 11.1
Difficulty Level: Hard

4. What is the relationship between alcohols I and II?

H CH3

CH3 H
OH H

H OH
I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
Ans: C

Topic: Structure and Nomenclature

Section: 5.12 and 11.1
Difficulty Level: Hard

5. What is the relationship between alcohols I and II?

H H

CH3 CH3
OH H

H OH
I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
Ans: D

705
Topic: Structure and Nomenclature
Section: 5.12 and 11.1
Difficulty Level: Hard

6. What is the relationship between alcohols I and II?

CH3

CH3

HO HO

I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
Ans: D

Topic: Structure and Nomenclature

Section: 5.12 and 11.1
Difficulty Level: Hard

7. What is the relationship between alcohols I and II?

CH3 CH3

OH
OH

I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
Ans: D

706
Topic: Nomenclature
Section: 11.1A
Difficulty Level: Easy

8. What is the correct IUPAC name for the following compound?

CH3
CH3CHOHCHCHCH(CH3)2
CH3
A) 4-isopropyl-3,4-dimethyl-2-butanol
B) 2,3,4-trimethyl-4-pentanol
C) 1,1,2,3-tetramethyl-4-pentanol
D) 3,4,5-trimethyl-2-hexanol
E) 3,4,5,5-tetramethyl-2-pentanol
Ans: D

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Easy

9. A correct IUPAC name for isobutyl alcohol is:

A) 2-Methyl-1-propanol
B) 2-Methyl-1-butanol
C) 1-Methyl-1-propanol
D) 1,1-Dimethyl-1-ethanol
E) 3-Methyl-1-propanol
Ans: A

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Easy

10. CH2CH3

CH3CH2COH

The IUPAC name of compound CH2CH3 is:

A) 1,1,1-Triethylmethanol
B) 1,1-Diethyl-1-propanol
C) 2-Ethyl-3-pentanol
D) 3-Ethyl-3-pentanol
E) tert-Heptanol
Ans: D

707
Topic: Nomenclature
Section: 11.1A
Difficulty Level: Medium

11. What is the correct IUPAC name for the following compound?
CH3
CH3CH2C=CCH2CH3
CH2CH2OH
A) 3-methyl-4-ethyl-3-hexen-6-ol
B) 4-ethyl-3-methyl-3,6-hexenol
C) 3-ethyl-4-methyl-3-hexen-1-ol
D) 3-methyl-4-(2-hydroxyethyl)-3-hexene
E) 3-(2-hydroxyethyl)- 3-methyl-3-hexene
Ans: C

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Medium

12. What is a correct IUPAC name for the following compound?

HO OH
A) 1,2-butanediol
B) isopropanol
C) 1-propanol
D) 1,2-propanediol
E) Ethylene glycol
Ans: D

708
Topic: Nomenclature
Section: 11.1A
Difficulty Level: Medium

13. What is a correct IUPAC name for the following compound?

HO OH

A) 1,2-butanediol
B) isopropanol
C) 1-proanol
D) Propylene glycol
E) 1,2-ethanediol
Ans: E

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Medium

14. The correct IUPAC name for tert-butyl alcohol is:

A) 1-Butanol
B) 2-Methyl-1-propanol
C) 2-Methyl-2-propanol
D) 2-Butanol
E) 1,1-Dimethyl-1-ethanol
Ans: C

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Medium

15. 2,2-Dimethyl-1-propanol has the common name:

A) Isoamyl alcohol
B) Isopentyl alcohol
C) tert-Pentyl alcohol
D) Neopentyl alcohol
E) 2-Methylisobutyl alcohol
Ans: D

709
Topic: Nomenclature
Section: 11.1A
Difficulty Level: Medium

16. Which of these, though often used, is an incorrect common name for CH3CHOHCH3?
A) Isopropyl alcohol
B) sec-Propyl alcohol
C) 2-Propanol
D) Isopropanol
E) More than one of these.
Ans: D

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Medium

17. Which of these, though often used, is an incorrect common name for (CH3)3COH?
A) tert-Butyl alcohol
B) tert-Butanol
C) 2-Methyl-2-propanol
D) More than one is incorrect.
E) Each is a correct name.
Ans: B

Topic: Isomerism, Stereoisomers

Section: 11.1A
Difficulty Level: Medium

18. Which of the following can be described as “optically active, primary alcohol”?
A) CH3CH2CH2CH2CH2OH
B) (CH3)2CHCH2CH2OH
C) CH3CH2CH(CH3)CH2OH
D) (CH3)2CHCHOHCH3
E) Two of the above
Ans: C

710
Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

19. OH

The correct IUPAC substitutive name for is:

A) 4-Penten-2-methyl-2-ol
B) 4-Methyl-1-penten-2-ol
C) 2-Methyl-4-penten-2-ol
D) 4-Methyl-1-penten-4-ol
E) 4-Hydroxy-4-methyl-1-pentene
Ans: C

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

20. OH

OH

is properly named:
A) cis-1,2-Cyclopentanediol
B) meso-1,2-Cyclopentanediol
C) (1R,2R)-1,2-Cyclopentanediol
D) (1R,2S)-1,2-Cyclopentanediol
E) (1S,2S)-1,2-Cyclopentanediol
Ans: C

711
Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

21. OH

OH

is properly named:
A) 1,2-Cyclopentanediol
B) 1,5-Cyclopentanediol
C) (1R,2R)-1,2-Cyclopentanediol
D) (1R,2S)-1,2-Cyclopentanediol
E) (1S,2S)-1,2-Cyclopentanediol
Ans: D

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

22. OH

OH

is properly named:
A) cis-1,2-Cyclohexanediol
B) meso-1,2-Cyclohexanediol
C) (1R,2R)-1,2-Cyclohexanediol
D) (1R,2S)-1,2-Cyclohexanediol
E) (1S,2S)-1,2-Cyclohexanediol
Ans: C

712
Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

23. OH

OH

is properly named:
A) 1,2-Cyclohexanediol
B) 1,6-Cyclohexanediol
C) (1R,2R)-1,2-Cyclohexanediol
D) (1R,2S)-1,2-Cyclohexanediol
E) (1S,2S)-1,2-Cyclohexanediol
Ans: D

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

24. OH

OH
is properly named:
A) 1,3-Cyclopentanediol
B) 1,4-Cyclopentanediol
C) (1R,3R)-1,3-Cyclopentanediol
D) (1R,3S)-1,3-Cyclopentanediol
E) (1S,3S)-1,3-Cyclopentanediol
Ans: C

713
Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

25. HO

OH
is properly named:
A) 1,4-Cycloheptanediol
B) 1,5-Cycloheptanediol
C) (1R,4R)-1,4-Cycloheptanediol
D) (1R,4S)-1,4-Cycloheptanediol
E) (1S,4S)-1,4-Cycloheptanediol
Ans: D

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

26. A correct name for the following Fischer projection formula is:
OH

H3C C C CH3

H
A) (R)-3-Pentyn-2-ol
B) (S)-3-Pentyn-2-ol
C) (R)-2-Pentyn-4-ol
D) (S)-2-Pentyn-4-ol
E) (S)-2-Hydroxy-3-pentyne
Ans: B

714
Topic: Stereoisomerism
Section: 11.1B
Difficulty Level: Easy

27. What is the relationship between alcohols I and II?

CH3

CH3

HO
OH

I II
They are:
A) different conformations of the same compound.
B) constitutional isomers.
C) enantiomers.
D) diastereomers.
E) identical.
Ans: B

715
Topic: Nomenclature
Section: 11.1B
Difficulty Level: Medium

28. Select the structure of benzyl methyl ether.

I CH3 O CH3

II CH3O

III CH3 O CH2

IV CH O CH
CH3 CH3

V CH3 CH2 O CH2 CH3

A) I
B) II
C) III
D) IV
E) V
Ans: C

Topic: Nomenclature
Section: 11.1B
Difficulty Level: Medium

29. Which is a correct IUPAC name for CH3CH2OCH2CH2CH2OCH2CH3?

A) 1,4-Dioxane
B) Ethylene glycol diethyl ether
C) 1,3-Diethoxypropane
D) 1,2-Diethoxyethane
E) 1,2-Diethoxymethane
Ans: C

716
Topic: Isomerism, Stereoisomers
Section: 11.1B
Difficulty Level: Medium

30. What is the total number of pentyl alcohols, including stereoisomers?

A) 7
B) 8
C) 9
D) 10
E) 11
Ans: E

Topic: Isomerism, Stereoisomers

Section: 11.1B
Difficulty Level: Medium

31. The number of primary alcohols corresponding to the formula C5H12O, counting
stereoisomers separately, is:
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: E

Topic: Isomerism, Stereoisomers

Section: 11.1B
Difficulty Level: Medium

32. The number of tertiary alcohols corresponding to the formula C5H12O, counting
stereoisomers separately, is:
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: A

717
Topic: Isomerism, Stereoisomers
Section: 11.1B
Difficulty Level: Medium

33. The number of secondary alcohols corresponding to the formula C5H12O, counting
stereoisomers separately, is:
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: E

Topic: Isomerism, Stereoisomers

Section: 11.1B
Difficulty Level: Medium

34. The total number of ethers corresponding to the formula C5H12O, counting
stereoisomers separately, is:
A) 4
B) 5
C) 6
D) 7
E) 8
Ans: D

Topic: Isomerism, Stereoisomers

Section: 11.1B
Difficulty Level: Medium

35. The number of optically active pentyl alcohols (C5H11OH), i.e., the total number of
individual enantiomers, is:
A) 0
B) 2
C) 3
D) 4
E) 6
Ans: E

718
Topic: Nomenclature
Section: 11.1B
Difficulty Level: Hard

36. What is the most accurate name for the molecule represented by the following Fischer
projection formula?
H
H3CH2C OCH3
CH3
A) sec-Butyl methyl ether
B) Isobutyl methyl ether
C) tert-Butyl methyl ether
D) (R)-2-Methoxybutane
E) (S)-2-Methoxybutane
Ans: E

Topic: Physical Properties, Comparison

Section: 11.2
Difficulty Level: Easy

37. Which of the compounds listed below would you expect to have the highest boiling
point? (They all have approximately the same molecular weight.)
A) CH3CH2CH2CH2CH3
B) CH3CH2CH2CH2OH
C) CH3CH2CH2OCH3
D) CH3CH2CH2Cl
E) CH3CH2OCH2CH3
Ans: B

Topic: Physical Properties, Comparison

Section: 11.2
Difficulty Level: Easy

38. Which compound would have the highest boiling point?

A) CH3CH2CH2CH3
B) CH3CH2OCH3
C) CH3CH2CH2OH
D) (CH3)2CHOH
E) HOCH2CH2OH
Ans: E

719
Topic: Physical Properties, Comparison
Section: 11.2
Difficulty Level: Easy

39. Which compound would have the lowest boiling point?

A) CH3CH2CH2CH3
B) CH3CH2OCH2CH3
C) CH3CH2CH2OH
D) (CH3)2CHOH
E) HOCH2CH2OH
Ans: A

Topic: Physical Properties, Comparison

Section: 11.2
Difficulty Level: Easy

40. Which compound would have the highest boiling point?

A) CH3CH2CH2CH3
B) CH2(OH)CH(OH)CH2OH
C) CH3CH2CH2OH
D) (CH3)2CHOH
E) HOCH2CH2OH
Ans: B

Topic: Physical Properties, Comparison

Section: 11.2
Difficulty Level: Easy

41. Which compound would have the lowest solubility in water?

A) Diethyl ether
B) Methyl propyl ether
C) 1-Butanol
D) 2-Butanol
E) Pentane
Ans: E

720
Topic: Physical Properties, Comparison
Section: 11.2
Difficulty Level: Easy

42. Which compound would have the greatest solubility in water?

A) Diethyl ether
B) Methyl propyl ether
C) 1-Butanol
D) 1,2-Butanediol
E) Pentane
Ans: D

Topic: Physical Properties, Comparison

Section: 11.2
Difficulty Level: Easy

43. Which compound would have the lowest boiling point?

OH CH2OH
OH OH
O

I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A

721
Topic: Physical Properties, Comparison
Section: 11.2
Difficulty Level: Easy

44. Which compound would have the highest boiling point?

O
O O O O

OH

I II III
OH
O

O OH

IV V

A) I
B) II
C) III
D) IV
E) V
Ans: E

Topic: Ether Reactivity

Section: 11.2
Difficulty Level: Easy

45. Which of the following statements is NOT true of ethers?

A) Ethers are generally unreactive molecules toward reagents other than strong acids.
B) Ethers generally have lower boiling points than alcohols of a corresponding molecular
weight.
C) Ethers generally have much lower water solubilities than alcohols with a corresponding
molecular weight.
D) Ethers can generally be cleaved by heating them with strong acids.
E) Ethers form peroxides when allowed to stand in the presence of oxygen.
Ans: C

722
Topic: General
Section: 11.3A
Difficulty Level: Easy

46. The major industrial process in use today for the production of methanol is the:
A) hydration of ethyne.
B) distillation of wood.
C) hydrogenation of carbon dioxide.
D) reduction of methanal.
E) catalytic reduction of carbon monoxide.
Ans: E

Topic: General
Section: 11.3B
Difficulty Level: Easy

47. Today, most industrial ethanol is made in the U.S. by the:

A) fermentation of grain.
B) hydrolysis of ethyl bromide.
C) hydration of ethylene.
D) reduction of acetaldehyde.
E) hydration of acetylene.
Ans: C

Topic: Ether Reaction Rates

Section: 11.3D
Difficulty Level: Easy

48. Which of these ethers is most resistant to peroxide formation on exposure to

atmospheric oxygen?
A) CH3OCH2CH3
B) CH3CH2OCH2CH3
C) (CH3)2CHOCH(CH3)2
D) (CH3)2CHOCH2CH3
E) CH3OC(CH3)3
Ans: E

723
Topic: Alcohol Synthesis
Section: 11.4
Difficulty Level: Easy

49. Which product(s) would you expect to obtain from the following sequence of reactions?
CH3
1. BH3-THF
?
2. H2O2, NaOH

CH3 CH3 H3C CH2OH

CH3 O
OH OH
OH

+ + +
enantiomer enantiomer enantiomer

I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C

724
Topic: Alcohol Synthesis
Section: 11.4
Difficulty Level: Easy

50. Select the structure of the major product formed from the following reaction.

CH3 1. Hg(OOCCH3)2
THF, H2O
?
2. NaBH4, NaOH

CH3 CH3 CH2OH HO CH3 CH3

OH

OH
OH

I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D

Topic: Alcohol Synthesis

Section: 11.4
Difficulty Level: Easy

51. Anti-Markovnikov hydration of the carbon-carbon double bond occurs when an alkene
reacts with:
A) BH3:THF; then H2O2/OH-
B) BH3:THF; then CH3COOH
C) Hg(OAc)2, THF, H2O; then NaBH4, OH-
D) Hg(OAc)2, THF, CH3OH; then NaBH4, OH-
E) Hg(OAc)2, THF, H2O; then BH3:THF
Ans: A

725
Topic: Reaction Mechanisms
Section: 11.4
Difficulty Level: Easy

52. Which statement is true concerning the formation of alcohols by the hydroboration-
oxidation sequence?
A) Overall, the process results in syn addition and anti-Markovnikov orientation.
B) Overall, the process results in anti addition and anti-Markovnikov orientation.
C) Overall, the process results in syn addition and Markovnikov orientation.
D) Overall, the process results in anti addition and Markovnikov orientation.
E) The stereochemistry and orientation are unpredictable.
Ans: A

Topic: Alcohol Synthesis

Section: 11.4
Difficulty Level: Medium

53. Which would be the best way to carry out the following synthesis?
?
CH3CH2CHCH3 CH3CH2CH2CH2OH

Br
A) (1) HA, heat; (2) H3O+, H2O, heat
B) (1) (CH3)3COK / (CH3)3COH; (2) BH3:THF, then H2O2, OH-
C) (1) (CH3)3COK / (CH3)3COH; (2) H3O+, then H2O, heat
D) (1) KOH, C2H5OH; (2) BH3:THF, then H2O2, OH-
E) (1) KOH, C2H5OH; (2) HA, heat; (3) H3O+, H2O, heat
Ans: B

726
Topic: Alcohol Synthesis, Mechanisms
Section: 11.4
Difficulty Level: Medium

54. Select the potential energy diagram that best represents the following reaction:

OH
H+
H2O

A) I
B) II
C) III
D) IV
E) V
Ans: D

727
Topic: Alcohol Synthesis
Section: 11.4
Difficulty Level: Medium

55. Which reaction can accomplish the following transformation in good yield:
?

OH
A) H+/H2O
B) oxymercuration/demercuation
C) hydroboration/oxidation
D) Reaction with NaOH
E) None of the above
Ans: B

Topic: Alcohol Synthesis, Isotope Labeling

Section: 11.4
Difficulty Level: Medium

56. The hydroboration-oxidation procedure can be successfully employed for synthesis of

deuterated derivatives, by using BD3 instead of BH3. What product would you expect
from the following reaction?

CH3
1. (BD3)2
?
2. H2O2/NaOH

HO D H D BD2 D D OH H BD2
H CH3 H CH3 H CH3 H CH3 D CH3

+ + + + +
enantiomer enantiomer enantiomer enantiomer enantiomer
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A

728
Topic: Alcohol Synthesis, Isotope Labeling
Section: 11.4
Difficulty Level: Medium

57. The oxymercuration-demercuration procedure can be successfully employed for

synthesis of deuterated derivatives, by using NaBD4 instead of NaBH4 in the second
step. What product would you expect from the following reaction?

1. Hg(OAc)2/H2O
?
2. NaBD4, NaOH

OH
OH D D OH

OH D OH

I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C

Topic: Alcohol Synthesis

Section: 11.4
Difficulty Level: Medium

58. Which of the following would be a reasonable synthesis of 2-butanol?

A) RCOOH
1-Butene
B) 1. BH3-THF
1-Butene
2. H2O2, NaOH
C) 1. Hg(OAc)2, THF, H2O
1-Butene
2. NaBH4, NaOH
D) 1. Ha(OAc)2/CH3OH
1-Butene
2. NaBH4, NaOH
E) None of these
Ans: C

729
Topic: Alcohol Synthesis
Section: 11.4
Difficulty Level: Medium

59. Which of the following would be a reasonable synthesis of CH 3CH2CH2CH2OH?

A) H3O+, heat
1-Butene
B) 1. BH3-THF
1-Butene
2. H2O2, NaOH
C) 1. Hg(OAc)2, THF, H2O
1-Butene
2. NaBH4, NaOH
D) 1. Ha(OAc)2/CH3OH
1-Butene
2. NaBH4, NaOH
E) None of these
Ans: B

Topic: Alcohol Synthesis

Section: 11.4
Difficulty Level: Medium

60. Which would be the major product of the reaction shown?

CH2CH3 1. Hg(OAc)2, THF, H2O

?
2. NaBH4, NaOH

H OH H H CH2CH3

CH2CH3
OHCH2CH3 H H CH2CH2OH H CH2CH3 O
H H H OH H

I II III IV V

A) I
B) II
C) III
D) IV
E) V
Ans: B

730
Topic: Alcohol Synthesis
Section: 11.4
Difficulty Level: Medium

61. What is the major product of the reaction:

i) BH3, THF
?
ii) H2O2,NaOH

CH3 CH3
CH3 OH OH CH3
OH

+ +
enantiomer enantiomer

I II III IV

A) I
B) II
C) III ****
D) IV
E) Both III and IV
Ans: D

Topic: Alcohol Synthesis

Section: 11.4
Difficulty Level: Medium

62. Oxymercuration-demercuration of 3-methylcyclopentene produces this/these product(s):

HO CH3 CH2OH CH3 CH3

OH

OH

I II III IV
A) I
B) II
C) III
D) IV
E) Both III and IV
Ans: E

731
Topic: Alcohol Synthesis
Section: 11.4
Difficulty Level: Hard

63. What is the major product of the reaction when (R)-3-methylcyclohexene is subjected to
the hydroboration-oxidation sequence?
A) (1R,2R)-2-methylcyclohexanol + (1S,2R)-2-methylcyclohexanol
B) (1S,2R)-2-methylcyclohexanol + (1S,2S)-2-methylcyclohexanol
C) (1R,3R)-3-methylcyclohexanol + (1S,3R)-3-methylcyclohexanol
D) (1S,3R)-3-methylcyclohexanol (1S,3S)-3-methylcyclohexanol
E) Two of the above
Ans: E

Topic: Alcohol Synthesis

Section: 11.4
Difficulty Level: Hard

64. Which would be the best method for converting 3,3-dimethyl-1-pentene into 3,3-
dimethyl-2-pentanol?
A) H3O+, heat
B) BH3:THF; then H2O2, OH-
C) concd. H2SO4; then H2O, heat
D) Hg(OAc)2/THF-H2O; then NaBH4,OH-
E) HBr; then NaOH/H2O
Ans: D

732
Topic: Alcohol Synthesis, Mechanisms
Section: 11.4
Difficulty Level: Hard

65. Assuming an overall exothermic process, select the potential energy diagram that best
represents the following reaction:

HO
H+
H2O

A) I
B) II
C) III
D) IV
E) V
Ans: E

733
Topic: Alcohol Synthesis
Section: 11.4
Difficulty Level: Hard

66. Select the structure of the major product formed from the following reaction.
H3O+
?

OH

OH

OH
II III
I

OH

OH

V
IV
A) I
B) II
C) III
D) IV
E) V
Ans: C

734
Topic: Alcohol Synthesis
Section: 11.4
Difficulty Level: Hard

67. Select the structure of the major product formed from the following reaction.
H3O+
?

OH

OH

OH
II III
I

OH

OH
IV
IV
A) I
B) II
C) III
D) IV
E) V
Ans: C

735
Topic: Reaction Mechanisms
Section: 8.6 and 11.4
Difficulty Level: Medium

68. What is the electrophilic species involved in the initial step of the reaction below?

OH
Hg(OAc)2
HgOAc
THF, H2O
+
A) OH
+
B) HgOAc
C) H3O+
D) THF
E) the THF/H2O complex
Ans: B

Topic: Reaction Mechanisms

Section: 8.6 and 11.4
Difficulty Level: Medium

69. What is the nucleophilic species involved in the initial step of the reaction below?

OH
Hg(OAc)2
HgOAc
THF, H2O
-
A) OH
B) Hg(OAc)2
C) H2O
D) cyclopentene
E) the THF/H2O complex
Ans: D

Topic: Alcohol Reaction Rates

Section: 11.8
Difficulty Level: Easy

70. Which of the alcohols listed below would you expect to react most rapidly with HBr?
A) CH3CH2CH2CH2CH2CH2OH
B) (CH3CH2)2CH2CH2OH
C) (CH3CH2)2CHOHCH3
D) CH3CH2CH2CH2CH2OH
E) (CH3CH2)2C(CH3)OH
Ans: E

736
Topic: Alcohol Reaction Rates
Section: 11.8
Difficulty Level: Medium

71. Which alcohol would undergo acid-catalyzed dehydration most rapidly?

A) 3,3-dimethyl-1-butanol
B) 2,2-dimethyl-1-butanol
C) 3,3-dimethyl-2-butanol
D) 2-methyl-2-butanol
E) All would undergo dehydration equally rapidly.
Ans: D

Topic: Alcohol Reactions

Section: 11.8A
Difficulty Level: Easy

72. Which of the following could not be used to synthesize 2-bromopentane efficiently?
A) 1-Pentene + HBr 
B) 2-Pentene + HBr 
C) 2-Pentanol + HBr 
D) 2-Pentanol + PBr3 
E) All of the above would afford good yields of 2-bromopentane.
Ans: B

Topic: Alcohol Reaction Rates

Section: 11.8A
Difficulty Level: Easy

73. Which of these alkyl halide syntheses is predicted to occur at the greatest rate?
A) CH3CH2CH2CH2OH + HI 
B) (CH3)2CHCH2OH + HBr 
C) CH3CHOHCH2CH3 + HCl 
D) CH3CHOHCH2CH3 + HBr 
E) (CH3)3COH + HI 
Ans: E

737
Topic: Reaction Mechanisms
Section: 11.8A
Difficulty Level: Easy

74. The following reaction,

HBr
CH3CH2CH2CH2OH CH3CH2CH2CH2Br + H2O
heat
is probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
Ans: B

Topic: Reaction Mechanisms

Section: 11.8A
Difficulty Level: Medium

75. The reaction between 1-pentanol and HBr to yield 1-bromopentanol is probably:

A) an SN1-type reaction involving the protonated alcohol as the substrate.

B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
Ans: B

Topic: Reaction Mechanisms

Section: 11.8A
Difficulty Level: Medium

76. The reaction between 2-methyl-2-pentanol and HBr to yield 2-bromo-2-methylpentane

is probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
Ans: A

738
Topic: Reaction Mechanisms
Section: 11.8A
Difficulty Level: Medium

77. The reaction between 2-methyl-2-pentanol and HBr to yield 2-methyl-2-pentene is

probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
Ans: C

Topic: Reaction Mechanisms

Section: 11.8A
Difficulty Level: Medium

78. The reaction between 4-methyl-1-pentanol and HBr to yield 4-methyl-1-pentene is

probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.
Ans: D

739
Topic: Alcohol Reactions, Mechanisms
Section: 11.8A
Difficulty Level: Medium

79. Assuming an overall exothermic process, select the potential energy diagram that best
represents the following reaction:

OH
H+
heat
(-H2O)

A) I
B) II
C) III
D) IV
E) V
Ans: B

740
Topic: Alcohol Reactions
Section: 11.8A
Difficulty Level: Medium

80. Which of the following could be used to synthesize 2-bromobutane?

A) CH3CH2CHCH2 + Br2 (aq) 
B) CH3CH2CCH3 + HBr 
C) CH3CH2CCH + HBr 
D) CH3CH2CCH + Br2 
E) More than one of the above
Ans: B

Topic: Alcohol Reactions

Section: 11.8A
Difficulty Level: Medium
81. Which of the following could be used to synthesize 2-iodobutane?
A) CH3CH2CHCH2 + I2 (aq) 
B) CH3CH2CCH3 + HI 
C) CH3CH2CCH + HI 
D) CH3CH2CCH + I2 
E) None of the above
Ans: B

Topic: Alcohol Reactions

Section: 11.8A
Difficulty Level: Medium
82. Which of the following could be used to synthesize 2-chlorobutane?
A) CH3CH2CHCH2 + Cl2 (aq) 
B) CH3CH2CCH3 + HCl 
C) CH3CH2CCH + HCl 
D) CH3CH2CCH + Cl2 
E) None of the above
Ans: B

741
Topic: Alcohol Reaction Rates
Section: 11.9
Difficulty Level: Easy

83. Which of the alcohols listed below would you expect to react most rapidly with PBr3 ?
A) CH3CH2CH2CH2CH2CH2OH
B) (CH3CH2)2CH(OH)CH2CH3
C) (CH3CH2)2CHOHCH3
D) (CH3CH2)3COH
E) (CH3CH2)2C(CH3)OH
Ans: A

Topic: Alcohol Reactions

Section: 11.9
Difficulty Level: Medium

84. Which of the following could be used to synthesize 1-bromobutane efficiently?

A) CH3CH2CH=CH2 + HBr 
B) CH3CH2CH2CH2OH + PBr3 
C) CH3CH2CH2(OH)CH3 + HBr 
D) CH3CH2CH2CH2OH + Br2 
E) None of these
Ans: B

Topic: Alcohol Reactions

Section: 11.9
Difficulty Level: Medium

85. Which of the following could be used to synthesize 1-bromopentane?

A) CH3CH2CH2CH=CH2 + HBr 
B) CH3CH2CH2CH2CH2OH + PBr3 
C) CH3CH2CH2CH2CH2OH + NaBr 
D) CH3CH2CH2CH2CH2OH + Br2 
E) CH3CH2CH2CH=CH2 + Br2 
Ans: B

742
Topic: Alcohol Reactions
Section: 11.9
Difficulty Level: Medium

86. CH3 CH3

H3C CH CH CH3 to H3C CH CH CH3

The conversion of OH Br is best

achieved through use of which of these reagents in a low temperature reaction?
A) Concd. HBr
B) Br2
C) NaBr, H2SO4
D) PBr3
E) HBr, peroxide
Ans: D

Topic: Alcohol Reactions

Section: 11.9
Difficulty Level: Medium

87. The conversion of 3-methyl-1-octanol to 1-chloro-3-methyloctane is best achieved

through use of which of these reagents?
A) Concd. HCl
B) SO2Cl2
C) NaCl, H2SO4
D) PCl3
E) POCl3
Ans: D

Topic: Reaction Mechanisms

Section: 11.9
Difficulty Level: Medium

88. The reaction between 4-methyl-1-pentanol and PBr3 to yield 1-bromo-4-methylpentane

is probably:
A) an SN1-type reaction involving the protonated alkyl dibomophosphite of the alcohol as
the substrate.
B) an SN2-type reaction involving the protonated alkyl dibomophosphite of the alcohol as
the substrate.
C) an E1-type reaction involving the protonated alkyl dibomophosphite of the alcohol as
the substrate.
D) an E2-type reaction involving the protonated alkyl dibomophosphite of the alcohol as
the substrate.
E) an epoxidation reaction.
Ans: B

743
Topic: Alcohol Reactions
Section: 11.8 and 11.9
Difficulty Level: Medium

89. Which of the following reactions would serve as a synthesis of butyl bromide?
A) reflux
CH3CH2CH2CH2OH + HBr
B) CH3CH2CH2CH2OH + PBr3 
C) reflux
CH3CH2CH2CH2OH + NaBr
D) CH3CH2CH2CH2OH + Br2 
E) Answers A) and B) only
Ans: E

Topic: Alcohol Reactions

Section: 11.8 and 11.9
Difficulty Level: Medium

90. Which reagent(s) would transform propyl alcohol into propyl bromide?
A) Concd. HBr and heat
B) PBr3
C) NaBr/H2O and heat
D) More than one of these
E) All of these
Ans: D

744
Topic: General
Section: 11.10
Difficulty Level: Easy

91. Which compound is a tosylate?

O O O
CH3 S O CH3 Br S O CH2 CH3 CH3 S O CH3

O O

I II III

O O
CH3 S CH3 CH3 O S CH3
O
IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A

745
Topic: Alcohol Reactions
Section: 11.10
Difficulty Level: Hard

92. What would be the major product of the following reaction sequence?

H
OH NaI
CH3SO2Cl
mesylate ?
CH3 base ethanol
H

H I H H
I H I OSO2I

CH3 CH3 CH3 CH3

H H I H
I II III IV
A) I
B) II
C) III
D) IV
E) An equimolar mixture of I and II
Ans: B

746
Topic: Alcohol Reactions
Section: 11.10
Difficulty Level: Hard

93. What would be the major product of the following reaction sequence?
OH
H
CH3SO2Cl NaI
mesylate ?
base ethanol
CH3
H

H I H H
I H I SO2I

CH3 CH3 CH3 CH3

H H I H
I II III IV

A) I
B) II
C) III
D) IV
E) An equimolar mixture of I and II
Ans: A

747
Topic: Alcohol Reactions
Section: 11.10
Difficulty Level: Hard

94. What would be the major product of the following reaction sequence?

OH
H
pCH3C6H4SO2Cl NaI
tosylate ?
base ethanol
CH3
H

I H H H
H I I SO2C6H4CH3

CH3 CH3 CH3 CH3

H H I H
I II III IV
A) I
B) II
C) III
D) IV
E) An equimolar mixture of I and II
Ans: B

748
Topic: Alcohol Reactions
Section: 11.10
Difficulty Level: Hard

95. What would be the major product of the following reaction sequence?

OH
H
pCH3C6H4SO2Cl NaBr
tosylate ?
base ethanol
CH3
H

H Br H H
Br H Br SO2C6H4CH3

CH3 CH3 CH3 CH3

Br H H H
I II III IV
A) I
B) II
C) III
D) IV
E) An equimolar mixture of II and III
Ans: C

749
Topic: Alcohol Reactions
Section: 11.10
Difficulty Level: Hard

96. What would be the major product of the following reaction sequence?
OH
H
pCH3C6H4SO2Cl NaOH
tosylate ?
base H2O
CH3
H

H OH H H
OH H OH SO2C6H4CH3

CH3 CH3 CH3 CH3

H H OH H
I II III IV

A) I
B) II
C) III
D) IV
E) An equimolar mixture of I and II
Ans: A

Topic: Alcohol Reactions

Section: 11.10
Difficulty Level: Hard

97. cis-3-Methylcyclopentanol is treated with CH3SO2 Cl in the presence of a base. The

product of the reaction then is allowed to react with KI in methanol. What is the final
product?
A) trans-1-Iodo-3-methylcyclopentane
B) cis-1-Iodo-3-methylcyclopentane
C) 1-Methylcyclopentene
D) 2-Methylcyclopentene
E) 3-Methylcyclopentene
Ans: A

750
Topic: Alcohol Reactions
Section: 11.10
Difficulty Level: Hard

98. The major product of the following reaction would be:

CH3
H OH CH3SO2Cl CH3CO2-
Product ?
base
C2H5

CH3 CH3 CH3

H3CCO2 H H O2CCH3 H3CCO2 OSO2CH3

C2H5 C2H5
C2H5

I II III
A) I
B) II
C) III
D) Equal amounts of I and II
E) None of these
Ans: A

Topic: Alcohol Reactions

Section: 11.10
Difficulty Level: Hard

99. trans-3-Methylcyclopentanol is treated with CH3SO2Cl in the presence of base. The

product of this reaction is then heated with KI in methanol. What is the final product?
A) trans-1-Iodo-3-methylcyclopentane
B) cis-1-Iodo-3-methylcyclopentane
C) 1-Methylcyclopentene
D) 2-Methylcyclopentene
E) 3-Methylcyclopentene
Ans: B

751
Topic: Alcohol Reactions/Stereochemistry
Section: 11.10
Difficulty Level: Hard

100. O

CH3 S OH,

Methanesulfonic acid, O is treated, in turn, with PCl5 and (R)-2-butanol.

Which of the following Fischer formulas is a stereochemically correct representation of
the final product?

CH3 H O CH3

MsO H MsO CH3 H3C S H

CH2CH3 CH2CH3 O CH2CH3

I II III

O H O CH3

H3C S CH3 H3C S Cl

O CH2CH3 O CH2CH3
IV V

A) I
B) II
C) III
D) IV
E) V
Ans: A

752
Topic: Reaction Mechanisms
Section: 11.11
Difficulty Level: Medium

101. The following reaction,

H2SO4
2 CH3CH2CH2CH2OH (CH3CH2CH2CH2)2O + H2O
heat
is probably:
A) an SN1-type reaction involving the protonated alcohol as the substrate.
B) an SN2-type reaction involving the protonated alcohol as the substrate.
C) an E1-type reaction involving the protonated alcohol as the substrate.
D) an E2-type reaction involving the protonated alcohol as the substrate.
E) an epoxidation reaction.

Ans: B

Topic: Ether Synthesis

Section: 11.11B
Difficulty Level: Medium

102. Which is the best way to prepare 3-methoxypentane via the Williamson method?
A) CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140C
B) CH3OH + (CH3)2CHCH2CH2OH + H2SO4, 140C
C) CH3ONa + (CH3CH2)2CHBr
D) CH3I + (CH3CH2)2CHONa
E) CH3I + (CH3)2CHCH2CH2ONa
Ans: D

Topic: Ether Synthesis

Section: 11.11B
Difficulty Level: Medium

103. Which method would provide the best synthesis of ethyl isopropyl ether?
A) (CH3)2CHONa + CH3CH2Br 
B) CH3CH2ONa + (CH3)2CHBr 
C) H2SO4, 140 oC
CH3CH2OH + (CH3)2CHOH
D) H2SO4, 180 oC
CH3CH2OH + (CH3)2CHOH
E) CH3CH2ONa + (CH3)2CHOH 
Ans: A

753
Topic: Ether Synthesis
Section: 11.11B
Difficulty Level: Medium

104. Which is the best method for the synthesis of tert-butyl methyl ether?
A) CH3ONa + (CH3)3CBr 
B) (CH3)3CONa + CH3I 
C) CH3OH + (CH3)3COH + H2SO4 at 140° C 
D) (CH3)3CONa + CH3OCH3 
E) CH3ONa + (CH3)3COH 
Ans: B

Topic: Ether Synthesis

Section: 11.11B
Difficulty Level: Hard

105. Which is the best method to prepare 2-ethoxy-5-methylhexane?

A) C2H5ONa + (CH3)2CHCH2CH2Br
B) C2H5ONa + (CH3)2CHCH2CH2CH2CH2Br
C) C2H5ONa + (CH3)2CHCH2CH2CHBrCH3
D) C2H5Br + (CH3)2CHCH2CH2CH(CH3)ONa
E) C2H5OH + (CH3)2CHCH2CH2CHOHCH3 + H2SO4, 140C
Ans: D

Topic: Ether Synthesis

Section: 11.11C
Difficulty Level: Hard

106. When 3-methyl-2-pentene is treated with mercuric acetate, Hg(O2CCH3)2, in a THF-

ethanol mixture and the resulting product reacted with NaBH 4 in basic solution, the
principal product formed is which of these?
A) 3-methyl-3-pentanol
B) 3-ethoxy-3-methylpentane
C) 3-methyl-2-pentanol
D) 2-ethoxy-3-methylpentane
E) 1-ethoxy-3-methylpentane
Ans: B

754
Topic: Ether Synthesis
Section: 11.11C
Difficulty Level: Hard

107. When 3-methyl-2-pentene is treated with mercuric acetate, Hg(O2CCH3)2, in a THF-t-

butyl alcohol mixture and the resulting product reacted with NaBH4 in basic solution,
the principal product formed is which of these?
A) 3-methyl-3-pentanol
B) 3-t-butoxy-3-methylpentane
C) 3-methyl-2-pentanol
D) 2- t-butoxy -3-methylpentane
E) 1- t-butoxy -3-methylpentane
Ans: B

Topic: Alcohol Reactions

Section: 11.11E
Difficulty Level: Medium

108. What is the product of the reaction of propyl alcohol with (CH 3)3SiCl in the presence of
a tertiary amine?
A) CH3CH2CH2Si(CH3)3
B) (CH3)2CHSi(CH3)3
C) CH3CH2CH2OSi(CH3)3
D) (CH3)2CHOSi(CH3)3
E) (CH3CH2CH2)3SiOH
Ans: C

755
Topic: Ether Reaction Rates
Section: 11.12
Difficulty Level: Easy

109. Which of these ethers is least likely to undergo significant cleavage by hot aqueous
H2SO4 ?

CH3OCH3 CH3OCH(CH3)2 (CH3)2CHOCH(CH3)2

I II III

(CH3)3COC(CH3)3 O

IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A

Topic: Chemical Tests

Section: 11.12
Difficulty Level: Medium

110. Which of the reagents listed below would serve as the basis for a simple chemical test to
distinguish between

and ?
O
A) AgNO3 in alcohol
B) NaOH in H2O
C) Br2 in CCl4
D) Cold concd. H2SO4
E) KMnO4 in H2O
Ans: D

756
Topic: Chemical Tests
Section: 11.12
Difficulty Level: Medium

111. Which of the reagents listed below would serve as the basis for a simple chemical test to
distinguish between

and ?
O Br
A) AgNO3 in C2H5OH
B) Dilute HCl
C) Br2 in CCl4
D) NaOH in H2O
E) KMnO4 in H2O
Ans: A

Topic: Ether Reactions

Section: 11.12A
Difficulty Level: Medium

112. The product(s) of the following reaction

excess HBr
is/are:
heat
O

O
and Br
OH

I II
Br

Br Br
and
OH Br

O
III
IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: C

757
Topic: Ether Reactions
Section: 11.12A
Difficulty Level: Medium

113. The product(s) of the following reaction

excess HI
is/are:
heat
O

O
and I
OH

I II
I

I I
and
OH I

O
III
IV

A) I
B) II
C) III
D) IV
E) None of these
Ans: C

758
Topic: Ether Reactions
Section: 11.12A
Difficulty Level: Medium

114. The product(s) of the following reaction

1 equiv. HI
is/are:
heat
O

O
and I
OH

I II
I

I
OH
O
III IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: C

759
Topic: Ether Reactions
Section: 11.12A
Difficulty Level: Medium

115. The product(s) of the following reaction

1 equiv. HI
is/are:
heat
O

I
O OH

I
II
I

I
OH

O
III IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: B

760
Topic: Ether Reactions
Section: 11.12A
Difficulty Level: Medium

116. The product(s) of the following reaction

1 equiv. HI
is/are:
heat
O

I
O OH

I
II
I

I
OH

O
III IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: C

761
Topic: Ether Reactions, Mechanisms
Section: 11.12A
Difficulty Level: Medium

117. Select the potential energy diagram that best represents the following reaction:

OCH3 I
HI
+ CH3OH

A) I
B) II
C) III
D) IV
E) V
Ans: E

762
Topic: Ether Reactions, Mechanisms
Section: 11.12A
Difficulty Level: Medium

118. Assuming an overall exothermic process, select the potential energy diagram that best
represents the following reaction:

HI
O OH + CH3I

A) I
B) II
C) III
D) IV
E) V
Ans: A

763
Topic: Ether Reactions
Section: 11.12A
Difficulty Level: Medium

119. What would be the major product(s) of the following reaction

Concd. HBr (xs)

C6H5CH2OCH3 ?
heat
A) C6H5Br + CH3OH
B) C6H5CH2Br + CH3Br
C) C6H5CH2OH + CH3Br
D) C6H5CH2Br + CH3OH
E) C6H5CH2CH2Br
Ans: B

Topic: Ether Reactions

Section: 11.12A
Difficulty Level: Medium

120. What would be the major product(s) of the following reaction

O 1 equiv. HBr(conc)
?
heat

A) C6H5Br + CH3OH
B) C6H5CH2Br + CH3Br
C) C6H5CH2OH + CH3Br
D) C6H5CH2Br + CH3OH
E) C6H5CH2CH2Br
Ans: D

764
Topic: Epoxide Synthesis
Section: 11.13
Difficulty Level: Medium

121. If cis-2-butene is treated with meta-chloroperbenzoic acid what is the final product?
O O O O

H H H CH3 H3C H H H

H3C CH3 H3C H H3C H H3CH2C H

I II III IV

A) I
B) II
C) III
D) IV
E) None of the above
Ans: A

Topic: Epoxide Synthesis

Section: 11.13
Difficulty Level: Medium

122. If trans-2-butene is treated with meta-chloroperbenzoic acid what is the final product?
O O O O

H H H CH3 H3C H H H

H3C CH3 H3C H H3C H H3CH2C H

I II III IV

A) I
B) II
C) III
D) IV
E) None of the above
Ans: B

765
Topic: Epoxide Synthesis
Section: 11.13
Difficulty Level: Medium

123. If (Z)-2-pentene is treated with meta-chloroperbenzoic acid what is the final product?
O O O

H H H CH3 H3C H

H3CH2C CH3 H3CH2C H H3CH2C H

I II III

A) I
B) II
C) III
D) All of the above
E) None of the above
Ans: A

Topic: Epoxide Synthesis

Section: 11.13
Difficulty Level: Medium

124. If (E)-2-pentene is treated with meta-chloroperbenzoic acid what is the final product?
O O O

H H H CH3 H3C H

H3CH2C CH3 H3CH2C H H3CH2C H

I II III

A) I
B) II
C) III
D) All of the above
E) None of the above
Ans: B

766
Topic: Epoxide Reactions, Isotope Labeling
Section: 11.14
Difficulty Level: Medium

125. Select the structure of the major product formed in the following reaction.
CH3CH CH2 HA
?
O 18
H2 O
18
A) CH3CH2CH2 OH
B) CH3CHCH3
18OH

C) CH3CHCH2OH
18OH

D) CH3CH CH2

OH 18OH
E) CH3CHCH218OH

18OH

Ans: C

Topic: Ether Reactions

Section: 11.14
Difficulty Level: Medium

126. Heating 2-ethoxyhexane with excess concentrated HBr would produce:

A) CH3CH2OCH2CH2CH2CH2CH2CH2Br
B) BrCH2CH2OCH2CH2CH2CH2CH2CH3
C) CH3CH2OH and CH3CH2CH2CH2CHBrCH3
D) CH3CH2Br and CH3CH2CH(OH)CH2CH2CH3
E) CH3CH2Br and CH3CH2CH2CH2CHBrCH3
Ans: E

767
Topic: Ether Reactions
Section: 11.14
Difficulty Level: Medium

127. Heating 2-ethoxyhexane with one equivalent of concentrated HBr would produce:
A) CH3CH2OCH2CH2CH2CH2CH2CH2Br
B) BrCH2CH2OCH2CH2CH2CH2CH2CH3
C) CH3CH2OH and CH3CH2CH2CH2CHBrCH3
D) CH3CH2Br and CH3CH2CH(OH)CH2CH2CH3
E) CH3CH2Br and CH3CH2CH2CH2CH(OH)CH3
Ans: E

Topic: Ether Reactions

Section: 11.14
Difficulty Level: Medium

128. Heating 2-ethoxyhexane with one equivalent of concentrated HI would produce:

A) CH3CH2OCH2CH2CH2CH2CH2CH2I
B) ICH2CH2OCH2CH2CH2CH2CH2CH3
C) CH3CH2OH and CH3CH2CH2CH2CHICH3
D) CH3CH2I and CH3CH2CH(OH)CH2CH2CH3
E) CH3CH2I and CH3CH2CH2CH2CH(OH)CH3
Ans: E

Topic: Epoxide Reactions

Section: 11.14
Difficulty Level: Medium

129. Epoxidation followed by reaction with aqueous base converts cyclopentene into which
of these?

H H OH
H
H OH H
OH
OH OH H
OH H OH

I II III IV
A) I
B) II
C) III
D) IV
E) Equal amounts of III and IV
Ans: E

768
Topic: Epoxide Reactions
Section: 11.14
Difficulty Level: Medium

130. What would be the major product of the following reaction sequence?
O

CH3O- H3O+
?
CH3OH

OH OCH3 OH OH OH
OCH3 OCH3 OCH
3

I II III IV
A) I
B) II
C) III
D) IV
E) Equal amounts of II and IV
Ans A

Topic: Epoxide Reactions

Section: 11.14
Difficulty Level: Medium

131. What would be the major product of the following reaction sequence?
O

H+
?
CH3OH

OH OCH3 OH OH OH
OCH3 OCH3 OCH
3

I II III IV
A) I
B) II
C) III
D) IV
E) Equal amounts of II and IV
Ans C

769
Topic: Epoxide Synthesis/Reactions
Section: 11.13 and 11.14
Difficulty Level: Hard

132. cis-3-Hexene is treated with meta-chloroperbenzoic acid and the product is then
subjected to acid-catalyzed hydrolysis. What is the final product?

CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CH3

H H H H H OH HO H H OH
H OH HO H HO H H OH H OH
CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CH3

I II III IV V
A) equal amounts I and II
B) equal amounts I, II and V
C) equal amounts III, IV and V
D) equal amounts III and IV
E) Only V
Ans: D

Topic: Epoxide Synthesis/Reactions

Section: 11.13 and 11.14
Difficulty Level: Hard

133. trans-3-Hexene is treated with meta-chloroperbenzoic acid and the product is then
subjected to acid-catalyzed hydrolysis. What is the final product?

CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CH3

H H H H H OH HO H H OH
H OH HO H HO H H OH H OH
CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CH3

I II III IV V
A) equal amounts I and II
B) equal amounts I, II and V
C) equal amounts III, IV and V
D) equal amounts, III and IV
E) Only V
Ans: E

770
Topic: Epoxide Synthesis and Reactions
Section: 11.13A and 11.14
Difficulty Level: Medium

134. What would be the final product?

O
CH3
RCOOH CH3OH, HA
H3CC CH2 product final product
A) (CH3)2CHCH2OCH3
B) (CH3)2CCH3

OCH3
C) (CH3)2CCH2OH

OCH3
D) (CH3)2CCH2OCH3

OH
E) (CH3)2CCH2OCH3

OCH3
Ans: C

Topic: Epoxide Synthesis/Reactions

Section: 11.13A and 11.14
Difficulty Level: Medium

135. What would be the major product of the following reaction sequence?
RCOOOH NH3
?

O OH OH OH NH2 NH2 OH

I II III IV
A) I
B) II
C) III
D) IV
E) Equal amounts of II and IV
Ans C

771
Topic: Epoxide Reactions
Section: 11.15
Difficulty Level: Hard

136. Which compound (or compounds) would be produced when trans-2-butene is treated
first with a peroxy acid to form an epoxide, and then the epoxide is subjected to acid-
catalyzed hydrolysis?

H CH3 CH3
HO CH3 HO H H OH
C C C

C C C
H CH3 HO CH3 H3C H
OH H OH

I II III
A) An equimolar mixture of I and II
B) An equimolar mixture of II and III
C) I alone
D) II alone
E) III alone
Ans: E

772
Topic: Epoxide Reactions
Section: 11.15
Difficulty Level: Hard

137. Which compound (or compounds) would be produced when cis-2-butene is treated first
with a peroxy acid to form an epoxide, and then the epoxide is subjected to acid-
catalyzed hydrolysis?

H CH3 CH3
HO CH3 HO H H OH
C C C

C C C
H CH3 HO CH3 H3C H
OH H OH

I II III
A) An equimolar mixture of I and II
B) An equimolar mixture of II and III
C) I alone
D) II alone
E) III alone
Ans: A

Topic: Nomenclature
Section: 11.16
Difficulty Level: Hard

138. What is the correct IUPAC name for the following compound?
O

O
A) 15-crown-5
B) 15-crown-4
C) 5-crown-15
D) 15-crown-15
E) Cyclopentadecane pentaether
Ans: A

773
Topic: Nomenclature
Section: 11.16
Difficulty Level: Hard

139. What is the correct IUPAC name for the following compound?
O

O O

A) 12-crown-5
B) 12-crown-4
C) 4-crown-12
D) 12-crown-12
E) Cyclododecane tetraether
Ans: B

SHORT ANSWER QUESTIONS

Topic: Isomers
Section: 11.1A
Difficulty Level: Medium

140. Draw all of the primary alcohols corresponding to the formula C 5H12O, including
stereoisomers.
Ans:
H H

OH OH OH

OH OH

774
Topic: Isomers
Section: 11.1A
Difficulty Level: Medium

141. Draw all of the enantiomeric forms corresponding to the formula C 5H12O.
Ans:
H H HO H HO H

OH OH

HO H HO H

Topic: Isomers
Section: 11.1A
Difficulty Level: Medium

142. Draw all the enantiomeric forms of ethers with the formula C 5H12O.
Ans:
O O

H H

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

143. Give the correct IUPAC name corresponding to the following structure:

OH

Ans: (R)-3-ethyl-2-methyl-3-hexanol

775
Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

144. Give the correct IUPAC name corresponding to the following structure:
Br H
CH3

OH
Ans: (1R,2R)-2-bromo-1-methylcyclopentanol

Topic: Nomenclature
Section: 11.1A
Difficulty Level: Hard

145. Give the correct IUPAC name corresponding to the following structure:

OH
Ans: 6-cyclohexyl-2,7-dimethyl-3-octanol

Topic: Isomerism
Section: 11.1B
Difficulty Level: Easy

146. Draw structures for all possible ethers having the formula C4H10O
Ans: O
O O

C4H10O: ethers

Topic: Isomers
Section: 11.1B
Difficulty Level: Medium

147. Draw all of the ethers corresponding to the formula C5H12O, including stereoisomers.
Ans:
O O
O
O

O O
O

H H

776
Topic: Nomenclature
Section: 11.1B
Difficulty Level: Hard

148. Give the correct IUPAC name corresponding to the following structure:

O O
Ans: 1,3-diethoxyhexane

Topic: Ether Reactivity

Section: 11.3D
Difficulty Level: Easy

149. Long-term storage of ethers can be dangerous, because most ethers react slowly with
oxygen by a radical process called __________________. This process forms peroxides
and hydroperoxides which are dangerously _______________.
Ans: autooxidation, explosive

Topic: General, Alcohol Synthesis

Section: 11.4
Difficulty Level: Easy

150. We have learned three different methods to convert alkenes into alcohols.
a. The method that takes place with Markovnikov regioselectivity but is prone to
rearrangement is ________________.
b. The method that takes place with Markovnikov regioselectivity and does not lead to
rearrangement is _____________.
c. The method that takes place with anti-Markovnikov regioselectivity and syn
stereoselectivity is _______________.
Ans: a. acid-catalyzed hydration; b. oxymercuration-demercuration; c. hydroboration-
oxidation

777
Topic: Alcohol Synthesis/Mechanism
Section: 11.4
Difficulty Level: Medium

151. What reaction is needed to accomplish the following transformation:

H3O+

OH
Ans:
Oxymercuration/demurcuration

Topic: Alcohol Synthesis/Mechanism

Section: 11.4
Difficulty Level: Hard

152. Propose a mechanism for the following transformation:

OH
H3O+

Ans:
H2O

H+
H

OH OH

-H+

778
Topic: Alcohol Synthesis
Section: 11.4
Difficulty Level: Hard

153. Draw the structures of all the products formed when (3R)-3-methylcyclopentene is
subjected to the hydroboration-oxidation sequence.
Ans: The alkene is symmetrically substituted: thus, Markovnikov rule does not apply.
Hence, all four products shown below are likely to be formed in roughly equal
proportions.

H3C H

hydroboration-oxidation

(3R)-3-methylcyclopentene

H3C H H3C H H3C H H3C H

OH OH
+ + +
OH OH

Topic: Alcohol Synthesis

Section: 11.4
Difficulty Level: Hard

154. Draw the products formed from the oxymercuration-demercuration of 3-

methylcyclopentene.
Ans:

OH and

OH

779
Topic: General, Alcohol Reactions
Section: 11.5
Difficulty Level: Easy

155. Reactions of alcohols can be broadly categorized into three types.

a. Those that utilize the hydroxyl oxygen as a ____________.
b. Those that utilize the hydroxyl proton as an _________.
c. Those that convert the hydroxyl group into a _____________.
Ans: nucleophile or base; b. acid; c. leaving group

Topic: Alcohol as Acids

Section: 11.6
Difficulty Level: Easy

156. Finish the following acid-base reaction and predict if it will proceed in the forward
direction:

OH + NaNH2

Ans:
Yes
OH + NaNH2 ONa + NH3

pKa = 18 pKa = 35

Topic: Alcohol as Acids

Section: 11.6
Difficulty Level: Easy

157. Finish the following acid-base reaction and predict if it will proceed in the forward
direction:

OH + Na+ C CH

Ans:
Yes
+ + HC CH
OH + Na C CH ONa

pKa = 25
pKa = 18

780
Topic: Alcohol as Acids
Section: 11.6
Difficulty Level: Easy

158. Finish the following acid-base reaction and predict if it will proceed in the forward
direction:

OH + CH3COONa

Ans:
No
CH3COONa ONa + CH3COOH
OH +

pKa = 5
pKa = 18

Topic: General
Section: 11.9
Difficulty Level: Medium

159. When an alcohol in which the OH is attached to a stereogenic carbon reacts with thionyl
chloride (SOCl2) in the presence of a 3° amine, the resulting alkyl chloride is produced
with _____________ of configuration.
Ans: inversion

Topic: General
Section: 11.10
Difficulty Level: Easy

160. Stereochemically speaking, conversion of an alcohol into a tosylate occurs with

_____________ of configuration.
Ans: retention

781
Topic: Multistep Reactions
Section: 11.10
Difficulty Level: Medium

161. Complete the following reaction sequence, giving structures for compounds C and D:

CH3SO2Cl CH3OH

DMF
C Na2CO3
D
OH

Ans:

C = D =
= OMs OCH3

Topic: Multistep Reactions

Section: 11.10
Difficulty Level: Medium

162. Supply the missing reagents A and B.

OH OTs CN
A B

CH3 CH3 CH3

Ans:
A pCH3C6H4SO2Cl, base B NaCN in ehtanol

Topic: General
Section: 11.11B
Difficulty Level: Easy

163. The SN2 reaction between an alkoxide and an alkyl halide is commonly referred to as
the _________________ synthesis.
Ans: Williamson

Topic: Ether Synthesis

Section: 11.11B
Difficulty Level: Easy

164. Which is the most efficient way to prepare isopropyl methyl ether via the Williamson
method?
Ans: CH3I + (CH3)2CHONa

782
Topic: Ether Synthesis/Mechanism
Section: 11.11B
Difficulty Level: Medium

165. Propose a mechanism for the following transformation:

Br -
OH
HO

Ans:
Br Br
H O O

-
OH O

Topic: Ether Synthesis

Section: 11.11B
Difficulty Level: Medium

166. Predict the product of the following reaction:

Br -
OH
HO

Ans:

783
Topic: Ether Synthesis/Mechanism
Section: 11.11B
Difficulty Level: Medium

167. Propose a mechanism for the following transformation:

HO Br -
OH

Ans:

O Br O
H Br

- O
OH

Topic: Ether Synthesis/Mechanism

Section: 11.11B
Difficulty Level: Medium

168. Propose a mechanism for the following transformation:

Br -
OH
HO

Ans:

Br Br
O O
H

O
-
OH

784
Topic: Ether Synthesis/Mechanism
Section: 11.11B
Difficulty Level: Medium

169. Propose a mechanism for the following transformation:

OH
OH
O

Br

Ans:

H OH
O
O

Br
Br

Topic: Ether Synthesis

Section: 11.11B
Difficulty Level: Medium

170. Which is the best method to prepare ethoxycyclopentane via the Williamson method?
Ans: ONa O
+ I

785
Topic: Ether Synthesis/Mechanism
Section: 11.11B
Difficulty Level: Medium

171. Propose a mechanism for the following transformation:

O I
1 equiv. HI
+ CH3OH
heat

Ans:
O O

H I H

CH2
I
I-
-CH3OH

Topic: Multistep Reactions

Section: 11.6 and 11.11B
Difficulty Level: Medium

172. Complete the following reaction sequence, giving structures for compounds A and B:

Nao CH3Br

DMF
A B
OH
-H2
Ans:

A = B =
= ONa OCH3

786
Topic: Multistep Reactions
Section: 11.11C
Difficulty Level: Medium

173. Supply the missing reagents A and B.

B OC(CH3)3
A

Ans:
A = Hg(OAc)2, THF, HOC(CH3)3 B = NaBH4

Topic: General
Section: 11.13
Difficulty Level: Easy

174. Three-membered rings containing oxygen are called _______________ or

______________.
Ans: oxiranes; epoxides

Topic: General
Section: 11.13B
Difficulty Level: Medium

175. A reaction which leads to a product of particular stereoisomeric outcome, depending on

the stereochemistry of the reactant, is termed_________________.
Ans: stereospecific

Topic: Epoxide Synthesis and Reactions

Section: 11.13 and 11.14
Difficulty Level: Hard

176. Provide a reasonable synthetic strategy for the synthesis of trans-1,2-

cyclohexanediol from bromocyclohexane
Ans
Br
: OH
CH3ONa m-CPBA +
H3O
O
CH3OH

OH

+ enantiomer

787
Topic: Epoxide Synthesis and Reactions
Section: 11.13 and 11.14
Difficulty Level: Hard

177. Provide a reasonable synthetic strategy for the synthesis of trans-2-

methoxycyclopentanol from bromocyclopentane
Ans:
Br OH

O
CH3ONa m-CPBA CH3ONa
OCH3
CH3OH CH3OH

+ enantiomer

Topic: General
Section: 11.16
Difficulty Level: Medium

178. The development of a procedure called __________________ has made the use of
nonpolar solvents possible in reactions involving polar reagents.
Ans: phase transfer catalysis

Topic: General
Section: 11.16
Difficulty Level: Medium

179. The relationship between a crown ether and the ion it transports is known as the
____________________ relationship.
Ans: guest-host

Topic: General
Section: 11.16
Difficulty Level: Medium

180. A compound or ion that prefers a nonpolar environment to an aqueous one is said to be
______________.
Ans: lipophilic

788
Topic: Spectroscopy of Alcohols
Section: Various
Difficulty Level: Medium

181. Propose a structure for the compound with the following formula that is consistent with
the IR and 1H NMR data shown:

C3H8O

IR – 3350cm−1, strong, broad

6H doublet at 1.3 , J = 7 Hz
1H singlet at 2.2 , (exchangeable)
1H septet at 4.0 , J = 7 Hz

Ans:

OH

Topic: Spectroscopy of Ethers

Section: Various
Difficulty Level: Medium

182. Propose a structure for the compound with the following formula that is consistent with
the IR and 1H NMR data shown:

C4H10O

IR – 1125cm−1, strong, broad

6H triplet at 1.2 , J = 7 Hz
4H quartet at 3.7 , J = 7 Hz

Ans:

789
Topic: Spectroscopy of Ethers
Section: Various
Difficulty Level: Medium

183. Propose a structure for the compound with the following formula that is consistent with
the IR and 1H NMR data shown:

C6H14O

IR – 1120cm−1, strong, broad

6H triplet at 0.9 
4H sextet at 1.5 
4H triplet at 3.4 

Ans:

Topic: Spectroscopy of Alcohols

Section: Various
Difficulty Level: Medium

184. Propose a structure for the compound with the following formula that is consistent with
the IR and 1H NMR data shown:

C7H8O

IR – 3325cm−1, strong, broad

1H broad singlet at 2.3  (exchangeable)
2H singlet at 4.6 
5H multiplet at 7.3 

Ans:
OH

790
Topic: Multistep Synthetic Strategy
Section: Various
Difficulty Level: Hard

185. Provide a reasonable synthetic strategy for the synthesis of a racemic mixture of
(1R,2R) and (1S,2S)-2-bromo-1-methylcyclopentanol from methylcyclopentane:
Ans: CH3
CH3 Br2 CH3ONa CH3
Br
h CH3OH
heat
Br2, H2O

Br H Br H
CH3 CH3
+
OH OH

(1R,2R) (1S,2S)
2-bromo-1-methylcyclopentanol

Topic: Multistep Synthetic Strategy

Section: Various
Difficulty Level: Hard

186. Provide a reasonable synthetic strategy for the synthesis of a racemic mixture of (1R,2R) and
(1S,2S)-2-bromo-1-methylcyclopentanol from methylenecyclopentane:
Ans: Br
HBr NaOCH3 Br2
HOCH3 H2O

Br H

+ enantiomer

OH

791
Topic: Multistep Reactions
Section: Various
Difficulty Level: Hard

187. Complete the following reaction sequence, giving structural details of all key
intermediates:
i) Li, NH3
?
ii) KMnO4 ,OH, H2O
iii) H3O+
Ans:
Li
NH3
i) KMnO4 ,OH, H2O
ii) H3O+

H OH HO H
+
H OH HO H
(2S,3S)-pentane-2,3-diol (2R,3R)-pentane-2,3-diol

792
Topic: Multistep Reactions
Section: Various
Difficulty Level: Hard

188. Complete the following reaction sequence, giving structural details of all key
intermediates:
i) P-2, H2
?
ii) KMnO4 ,OH, H2O
iii) H3O+
P-2, H2

i) KMnO4 ,OH, H2O

ii) H3O+
H OH HO H
+
HO H H OH

Ans: (2S,3R)-pentane-2,3-diol (2R,3S)-pentane-2,3-diol

Topic: Multistep Reactions

Section: Various
Difficulty Level: Hard

189. Complete the following reaction sequence, giving structural details of all key intermediates:
i) Lindlar catalyst, H2
?
ii) KMnO4 ,OH, H2O
iii) H3O+ Ans:
Lindlar catalyst
H2

i) KMnO4 ,OH, H2O

ii) H3O+
H OH HO H
+
HO H H OH
(2S,3R)-pentane-2,3-diol (2R,3S)-pentane-2,3-diol

793
Topic: Multistep Reactions
Section: Various
Difficulty Level: Hard

190. Complete the following reaction sequence, giving structural details of all key
intermediates:
i) Lindlar catalyst, H2
?
ii) OsO4
iii) NaHSO3
i) Lindlar catalyst
H2

ii) OsO4
iii) NaHSO3

H OH HO H
+
HO H H OH
(2S,3R)-pentane-2,3-diol (2R,3S)-pentane-2,3-diol

Topic: Multistep Reactions

Section: Various
Difficulty Level: Hard

191. Complete the following reaction sequence, giving structural details of all key
intermediates:
i) H2, Lindlar catalyst
?
ii) KMnO4 ,OH, H2O
iii) H3O+
Ans: H OH

H2 i) KMnO4 ,OH , H2O
Lindlar ii) H3O+ HO H
catalyst
meso

794
Topic: Multistep Reactions
Section: Various
Difficulty Level: Hard

192. Complete the following reaction sequence, giving structural details of all key
intermediates:
i) H2, P-2
ii) KMnO4 ,OH, H2O ?
iii) H3O+

Ans: H OH
H2, P-2 
i) KMnO4 ,OH , H2O
ii) H3O+ HO H
meso

Topic: Multistep Reactions

Section: Various
Difficulty Level: Hard

193. Complete the following reaction sequence, giving structural details of all key
intermediates:
i) Li, NH3
ii) m-CPBA ?
iii) H3O+, H2O
Ans:
Li
NH3
i) m-CPBA
ii) H3O+, H2O

HO H H OH
+
H OH HO H
(2R,3S)-pentane-2,3-diol (2S,3R)-pentane-2,3-diol

795
Topic: Spectroscopy of Ethers
Section: Various
Difficulty Level: Hard

194. Propose a structure for the compound with the following formula that is consistent with
the IR and 1H NMR data shown:

C6H14O

IR – 1120cm−1, strong, broad

3H triplet at 1.1 
9H singlet at 1.15 
2H quartet at 3.45 

Ans:

796
Topic: Spectroscopy of Ethers
Section: Various
Difficulty Level: Hard

195. A compound has the formula C5H10, with the 13C and 1H NMR spectral data shown.
Propose structure that fits this data.
13
C NMR
Broadband decoupled 13C NMR: 23.5, 26.7, 68.9 δ
DEPT-90: no peaks
DEPT-135: no positive peaks; negative peaks at 23.5, 26.7, 68.9 δ
1
H NMR
1.7 δ, multiplet (6H)
3.72 δ, triplet (4H) J = 7Hz

Ans:

797
Topic: Spectroscopy of Alcohols
Section: Various
Difficulty Level: Hard

196. A compound has the formula C6H14O. The 13C and 1H NMR spectral data for this
compound are:
13
C NMR
Broadband decoupled 13C NMR: 29.7, 29.8, 46.4, 60.0 δ
DEPT-90: no peaks
DEPT-135: positive peak at 29.8 δ; negative peaks at 29.7, 60.0 δ
1
H NMR
0.91 δ, singlet (9H)
1.53 δ, triplet (2H) J = 7.3Hz
2.13 δ, broad singlet (exchangeable, 1H)
3.70 δ, triplet (2H) J = 7.3Hz

Ans:

OH

798