Chapter Thirteen
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Easy
1. What is the IUPAC name for the following compound?
CH3
CH3
CH3CHCHCHCHCH3
OH
A)
B)
C)
D)
E)
CH3
4-isopropyl-3,4-dimethyl-2-butanol
2,3,4-trimethyl-4-pentanol
1,1,2,3-tetramethyl-4-pentanol
3,4,5-trimethyl-2-hexanol
3,4,5,5-tetramethyl-2-pentanol
Ans: D
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Easy
2.
A)
B)
C)
D)
E)
What is the IUPAC name for isobutyl alcohol?
2-methyl-1-propanol
2-methyl-1-butanol
1-methyl-1-propanol
1,1-dimethyl-1-ethanol
3-methyl-1-propanol
Ans: A
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Easy
3. What is the IUPAC name for the following compound?
CH2CH3
CH3CH2CCH2CH3
OH
A)
B)
C)
D)
E)
1,1,1-triethylmethanol
1,1-diethyl-1-propanol
2-ethyl-3-pentanol
3-ethyl-3-pentanol
t-heptanol
Ans: D
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
4.
A)
B)
C)
D)
E)
What is the IUPAC name for t-butyl alcohol?
1-butanol
2-methyl-1-propanol
2-methyl-2-propanol
2-butanol
1,1-dimethyl-1-ethanol
Ans: C
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
5. What is the IUPAC name for the following compound?
OH
A)
B)
C)
D)
E)
1-isopropyl-4-cyclopentanol
3-isopropylcyclopentanol
1-isopropyl-3-cyclopentanol
1-isopropyl-4-hydroxycyclopentane
None of these
Ans: B
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
6. What is the correct structure for 1-chloro-3-ethyl-2-pentanol?
CH2CH3
CH2CH3
CH3CH2CCH2CH2Cl
CH3CHCHCH2CH2Cl
OH
OH
I
A)
B)
C)
D)
E)
II
CH3CH2CHCH2CHCl CH3CH2CHCHCH2Cl
III
I
II
III
IV
None of these
Ans: D
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
7. What is the IUPAC name for the following compound?
Br
HO
A)
B)
C)
D)
E)
2-methyl-5-bromocyclohexanol
3-bromo-2-methylcyclohexanol
1-bromo-4-methylcyclohexanol
4-bromo-6-methylcyclohexanol
4-bromo-2-methylcyclohexanol
Ans: E
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
CH2CH3
CH2CH3
OH
IV
OH
8. What is the IUPAC name for the following compound?
CH2CH2OH
CH3CH2C=CCH2CH3
CH3
A)
B)
C)
D)
E)
3-methyl-4-ethyl-3-hexen-6-ol
4-ethyl-3-methyl-3,6-hexenol
3-ethyl-4-methyl-3-hexen-1-ol
3-methyl-4-(2-hydroxyethyl)-3-hexene
3-(2-hydroxyethyl)- 3-methyl-3-hexene
Ans: C
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
9. What is the IUPAC name for the following compound?
OH
A)
B)
C)
D)
E)
4-penten-2-methyl-2-ol
4-methyl-1-penten-2-ol
2-methyl-4-penten-2-ol
4-methyl-1-penten-4-ol
4-hydroxy-4-methyl-1-pentene
Ans: C
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
10. What is the IUPAC name for the following compound?
CH3
H
HO
C
C
CC
H
2 CH
3
A)
B)
C)
D)
E)
(R)-3-hexyn-2-ol
(S)-3-hexyn-2-ol
(R)-2-hexyn-4-ol
(S)-2-hexyn-4-ol
(S)-2-hydroxy-3-hexyne
Ans: B
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
11. What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?
OH
Br
Br
Br
Br
CH3CCH2CH2CH2CHOH
CH3CH2CH2CH2CCH(CH3)OH
I
Br
Br
III
II
OH
OH
Br
Br
Br
Br
IV
A)
B)
C)
D)
E)
CH3
V
I
II
III
IV
V
Ans: D
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
12. What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?
OH
HO
I
III
II
OH
HO
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: E
IV
V
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
13. What is the IUPAC name for the following compound?
OH
Ans: 7-ethyl-8-methyl-4-nonanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
14. What is the IUPAC name for the following compound?
HO
Ans: (R)-3-ethyl-2-methyl-3-heptanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
15. What is the IUPAC name for the following compound?
Br
OH
Ans: (1R,2S)-2-bromo-1-methylcyclopentanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
16. What is the IUPAC name for the following compound?
OH
Ans: 7-cyclohexyl-2,8-dimethyl-3-decanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
17. Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol?
Ans:
OH
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
18. Provide the structure for 5-chloro-2-propyl-1-heptanol.
Cl
Ans:
OH
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
19. Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.
Ans:
OH
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
20. What is the IUPAC name for the following compound?
OH
Ans: 4-isobutyl-2-methyl-3-octanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Hard
21. What is the IUPAC name for the following compound?
HO
H
C
CH3(CH2)4
C
C
H
Ans: (S)-1-octyn-3-ol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
22. What is the IUPAC name for the following compound?
HO
Ans: 4,5,6-tripropyl-4-decanol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
23. What is the IUPAC name for the following compound?
HO
Ans: 3-ethyl-3-cyclohexenol
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Easy
24. What is the correct structure for 2-methylphenol?
HO
A)
B)
C)
D)
E)
OH
OH
I
II
OH
OH
III
IV
V
I
II
III
IV
V
Ans: A
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
25. What is the correct structure for 2-bromo-5-isopropylphenol?
OH
Br
OH
OH
OH
Br
IV
V
Br
Br
Br
I
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: B
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
II
III
OH
26. What is the IUPAC name for the following compound?
OH
Br
Br
A)
B)
C)
D)
E)
3,4-dibromophenol
2,4-dibromophenol
2,5-dibromophenol
3,6-dibromophenol
2,6-dibromophenol
Ans: C
Topic: Nomenclature of alcohols
Section: 13.1
Difficulty Level: Medium
27. What is the IUPAC name for the following compound?
OH
Ans: 2-sec-butyl-5-ethylphenol
Topic: Nomenclature of alcohols
Section: 13.5
Difficulty Level: Medium
28. What is the IUPAC name for the following compound?
HOCH2CH2CH2OH
A) 1,2-butanediol
B) isopropanol
C) 1-propanol
D) 1,3-propanediol
E) 1,2-ethanediol
Ans: D
Topic: Nomenclature of alcohols
Section: 13.5
Difficulty Level: Hard
29. What is the IUPAC name for the following compound?
OH
OH
A)
B)
C)
D)
E)
cis-1,2-cyclopentanediol
meso-1,2-cyclopentanediol
(1R,2R)-1,2-cyclopentanediol
(1R,2S)-1,2-cyclopentanediol
(1S,2S)-1,2-cyclopentanediol
Ans: E
Topic: Nomenclature of alcohols
Section: 13.5
Difficulty Level: Hard
30. What is the IUPAC name for the following compound?
OH
OH
Ans: 3,5-dimethyl-2,4-heptanediol
Topic: Nomenclature of alcohols
Section: 13.5
Difficulty Level: Hard
31. Provide the structure for (2R,3S)-2-bromo-1,3-pentanediol.
OH
Ans:
OH
Br
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Hard
32. Explain why cyclohexanol has a pKa of 18 and phenol has a pKa of 10. Use structural
drawings to explain your reasoning.
Ans: The conjugate base of phenol is resonance stabilized. The negative charge on
oxygen is delocalized over the aromatic ring. This makes the conjugate base more
stable and thus a weaker base, making phenol a stronger acid.
O
O
O
O
The conjugate base of cyclohexanol has no resonance stabilization and the
negative charge on oxygen is localized, making it a stronger base, and
cyclohexanol a weaker acid
O
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Medium
33. Rank the following alcohols in decreasing order of acidity.
Br
I
Ans: II>I>III
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Medium
OH
OH
OH
F
II
I
III
34. Which one of the following alcohols is most acidic?
O
OH
O
OH
OH
III
II
I
Ans: I
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Medium
35. Rank the following alcohols in decreasing order of acidity. Explain your answer.
F
F
OH
OH
OH
F
F
III
II
I
Ans: I>III>II
The negative charge on the conjugate base of compound I is stabilized by three
electron withdrawing fluorine atoms via inductive effect, making it the weakest
base and the alcohol strongest acid.
The negative charge on the conjugate base of compound II is not stabilized, as it
does not have any electronegative atoms on the carbon chain, making it a stronger
base and the alcohol weakest acid.
The negative charge on the conjugate base of compound III is less stabilized than
I, because it has only one fluorine atom connected. Thus making it a stronger acid
than II, but a weaker acid than I.
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Medium
36. Rank the following alcohols in decreasing order of acidity.
O2N
OH
I
Ans: I>III>II
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Medium
OH
II
NC
OH
III
37. Predict the product(s) for the following reaction.
OH
Na
ONa
Ans:
+
1
H2
2
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Medium
38. Predict the product(s) for the following reaction.
OH
Li
Ans:
O Li
+
1
H2
2
Topic: Acidity of alcohols and phenols
Section: 13.2
Difficulty Level: Medium
39. Predict the product for the following reaction.
OH
1. NaH
2. CH3CH2Br
Ans:
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Medium
O
40. Provide the reagents necessary to carry out the following conversion.
CH3CH2CH2CHCH3
CH3CH2CH2CH2CH2OH
Br
Ans: 1. (CH3)3COK
2. BH3•THF
3. H2O2/NaOH/H2O
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Medium
41. Predict the product(s) for the following reaction.
1. BH3 THF
2. H2O2/NaOH/H2O
CH2OH
OH
OH
+ enantiomer
I
A)
B)
C)
D)
E)
I
II
III
IV
None of these
Ans: B
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Medium
OH
+ enantiomer
II
III
IV
42. Predict the product for the following reaction.
1. Hg(OAc)2, H2O
2. NaBH4
CH2OH
OH
OH
II
I
A)
B)
C)
D)
E)
OH
III
IV
I
II
III
IV
None of these
Ans: C
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Medium
43. Provide the reagents necessary to carry out the following conversion.
(E)-3-methyl-3-hexene
Ans: H3O+
OR
1. Hg(OAc)2, H2O
2. NaBH4
3-methyl-3-hexanol
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Medium
44. Predict the major product for the following reaction.
H3O+
Ans:
OH
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Medium
45. Predict the product for the following reaction.
1. Hg(OAc)2, H2O
2. NaBD4
OH
OH
I
A)
B)
C)
D)
E)
OH
OH
D
III
II
D
D
OH
IV
V
I
II
III
IV
V
Ans: C
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Medium
46. Provide the reagents necessary to carry out the following conversion.
Br
Ans: NaOH
Topic: Preparation of Alcohols
Section: 13.3
Difficulty Level: Hard
OH
47. Provide the reagents necessary to carry out the following conversion.
OH
Cl
A)
B)
C)
D)
E)
NaOH/H2O
1. NaOCH3, 2. H3O+
1. (CH3)3COK, 2. BH3•THF, 3. H2O2/NaOH/H2O
1. (CH3)3COK, 2. H3O+
B&D
Ans: D
Topic: Oxidation states
Section: 13.4
Difficulty Level: Easy
48. What is the oxidation state of the carbon atoms I and II in the following compound?
O
II
H
I
A)
B)
C)
D)
E)
O
I. +1, II. +2
I. +2, II. +2
I. +1, II. +3
I. +3, II. +2
I. +2, II. +1
Ans: E
Topic: Oxidation states
Section: 13.4
Difficulty Level: Easy
49. What is the oxidation state of the carbon atoms I and II in the following reaction?
O
CH3CH
I
A)
B)
C)
D)
E)
I. +1, II. +2
I. +2, II. +2
I. +1, II. +3
I. +3, II. +2
I. +2, II. +1
Ans: C
O
CH3COH
II
Topic: Oxidation states
Section: 13.4
Difficulty Level: Medium
50. For the following conversion, identify if the starting material has been oxidized, reduced
or neither. Explain your answer.
OH
O
Ans: Oxidized.
The carbon atom bonded to OH in the starting compound has a zero oxidation
state and the carbonyl carbon atom in the product has an oxidation state of +2.
Topic: Oxidation states
Section: 13.4
Difficulty Level: Medium
51. For the following conversion, identify if the starting material has been oxidized, reduced
or neither.
Cl
Cl
Ans: Oxidized.
Topic: Oxidation states
Section: 13.4
Difficulty Level: Medium
52. For the following conversion, identify if the starting material has been oxidized, reduced
or neither. Explain your answer.
OH
O
Ans: Neither.
The oxidation state of the carbon atoms is not changed.
Topic: Oxidation states
Section: 13.4
Difficulty Level: Hard
53. For the following conversion, identify if the starting material has been oxidized, reduced
or neither.
O
H
O
A)
B)
C)
D)
reduced
oxidized
neither
A&B
Ans: B
Topic: Oxidation states
Section: 13.4
Difficulty Level: Hard
54. For the following conversion, identify if the starting material has been oxidized, reduced
or neither.
OH
O
A)
B)
C)
D)
O
O
reduced
oxidized
neither
A&B
Ans: C
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Easy
55. Predict the product for the following reaction.
O
NaBH4/CH3OH
CH3CCH2CH2CH3
OH
Ans:
CH3CHCH2CH2CH3
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Medium
56. Predict the product for the following reaction.
O
H
NaBH4/CH3OH
O
OH
OH
II
I
A)
B)
C)
D)
OH
OH
OH
IV
III
I
II
III
IV
Ans: A
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Medium
57. Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4
followed by water?
O
O
O
H
I
II
O
O
H
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: A
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Hard
V
III
58. Provide the reagents necessary to carry out the following conversion.
OH
HC
CH3CHCH2CH2CH3
CCH2CH2CH3
+
Ans: 1. H3O / HgSO4
2. NaBH4/CH3OH
OR
1. H2/Ni2B (OR Na, NH3)
2. H3O+
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Hard
59. Predict the product for the following reaction.
O
H
H2.Pd
O
OH
I
A)
B)
C)
D)
OH
OH
OH
II
I
II
III
IV
Ans: C
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Hard
III
OH
IV
60. Predict the product for the following reaction.
O
COCH3
NaBH4 / H2O
O
O
Ans:
COCH3
H
HO
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Hard
61. Predict the product for the following reaction.
O
COCH3
1. LiAlH4 excess
2. H2O
O
CH2OH
Ans:
H
HO
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Hard
62. Predict the product for the following reaction.
H2O / H2SO4
NaBH4/CH3OH
HgSO4
Ans:
OH
Topic: Preparation of Alcohols via Reduction
Section: 13.4
Difficulty Level: Medium
63. Provide the reactant (A) for the following reaction
1. LiAlH4
5-methyl-3-heptanol
A
2. H2O
O
O
O
H
I
II
O
O
III
H
IV
A)
B)
C)
D)
E)
V
I
II
III
IV
V
Ans: A
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Easy
64. Provide the reagents necessary to carry out the following conversion.
A)
B)
C)
D)
E)
cyclohexene
KMnO4, NaOHcold
KMnO4, H3O+, 75oC
H2SO4, heat
1. mCPBA 2. H3O+
none of these
Ans: A
cis-1,2-cyclohexanediol
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Medium
65. Predict the product(s) for the following reaction sequence.
H2/Ni2B
1. OsO4
3-hexyne
2. NaHSO3
H
HO
A)
B)
C)
D)
E)
HO
OH
H
I
HO
HO
H
H
II
H
OH
H
III
I
II
III
Both I & II
None of these
Ans: A
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Medium
66. Provide the reagents necessary to carry out the following conversion.
A)
B)
C)
D)
E)
cyclohexene
KMnO4, NaOH
KMnO4, H3O+, 75oC
H2SO4, heat
1. mCPBA 2. H3O+
none of these
Ans: D
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Medium
trans-1,2-cyclohexanediol
67. Provide the structure of each product (A-D) in the following reaction sequence.
CH3CH2ONa
mCPBA
A
B
Br2
C
NaOH/H2O
D
h
CH3
CH3
Ans:
Br
OH
O
OH
+ enantiomer
+ enantiomer
A
C
B
H
D
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Hard
68. Predict the product for the following reaction.
O
O
excess
H
OH
NaBH4/CH3OH
OH
O
O
OH
OH
H
II
I
OH
III
OH
OH
OH
OH
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: C
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Medium
V
69. Predict the product(s) for the following reaction.
O
H3O+
OH
OH
H
O
OH
I
A)
B)
C)
D)
E)
OH
OH
II
IV
III
I
II
III
IV
none of these
Ans: C
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Medium
70. Provide the reagent(s) necessary to carry out the following conversion.
OH
OH
Ans: 1. mCPBA
2. H3O+ OR NaOH/H2O
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Hard
71. Provide the reagent(s) necessary to carry out the following conversion.
OH
OH
Ans: 1. O3
2. (CH3)2S
3. excess NaBH4/CH3OH
Topic: Preparation of Diols
Section: 13.5
Difficulty Level: Hard
72. Predict the product(s) for the following reaction.
O
1. excess LiAlH4
O
2. H2O
O
Ans:
OH
OH
OH
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Easy
73. Predict the product for the following reaction sequence.
O
1. CH3CH2MgBr
2. H2O
Ans:
HO
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Medium
74. Predict the product for the following reaction sequence.
O
1.
Mg/ether
H
Br
2. H2O
Ans:
OH
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Medium
75. Provide the reagent(s) necessary to carry out the following conversion.
O
O
Ans: 1. excess CH3MgBr/ether
2. H2O
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Medium
OH
76. Predict the product for the following reaction.
O
1. CH3CH2CH2MgBr/ether
2. H2O
OH
OH
HO
OH
I
A)
B)
C)
D)
E)
III
II
I
II
III
IV
None of these
Ans: A
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Medium
77. Predict the product for the following reaction.
O
Br
1.
Mg/ether
H
H
2. H2O
Ans:
OH
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Medium
IV
78. Using Grignard reaction, show how you could prepare the following alcohol.
OH
Ans:
MgBr
1.
O
C
H
H
2. H2O
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Medium
79. Using Grignard reaction, show how you could prepare the following alcohol.
OH
Ans:
1. MgBr
2. H2O
O
OR
1.
MgBr
O
2. H2O
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Hard
80. Using Grignard reaction, show how you could prepare the following alcohol.
HO
Ans:
MgBr
1.
O
2. H2O
OR
1.
O
MgBr
2. H2O
OR
1.
O
MgBr
2. H2O
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Hard
81. Provide the reagent(s) necessary to carry out the following conversion.
HO
Ans: 1. HBr
2. Mg/ether
O
3. H
4. H2O
H
Topic: Preparation of Alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Hard
82. Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard
reaction.
O
Ans:
MgBr
1.
2. H2O
Topic: Preparation of alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Medium
83. Predict the product for the following reaction.
O
OCH3
excess
1. CH3CH2CH2MgBr
2. H2O
Ans:
OH
Topic: Preparation of alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Hard
84. Predict the product for the following reaction.
O
O
excess
1. CH3CH2MgBr
2. H2O
Ans:
OH
OH
Topic: Preparation of alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Hard
85. Predict the product for the following reaction.
excess
1. CH3CH2MgBr
O
O
2. H2O
O
Ans:
OH
Topic: Preparation of alcohols via Grignard Reagents
Section: 13.6
Difficulty Level: Hard
86. Predict the product for the following reaction and provide a curved arrow mechanism
for the formation of the product.
excess
1. CH3CH2MgBr
O
O
2. H2O
O
Ans:
OH
Mechanism
O
O
O
CH3CH2MgBr
O
O
O
CH3CH2MgBr
O
O
+ CH3OMgBr
O
O
CH3CH2MgBr
O
+ CH3OMgBr
O
H
O
H
HO
+ OH
Topic: Protection of alcohols
Section: 13.7
Difficulty Level: Hard
87. Provide the reagent(s) necessary to carry out the following conversion.
OH
HO
Br
HO
Ans: 1. (CH3)3SiCl / (CH3CH2)3N
2. Mg/ether
O
3.
4. H2O
5. TBAF
Topic: Protection of alcohols
Section: 13.7
Difficulty Level: Hard
88. Provide the reagent(s) necessary to carry out the following conversion.
OH
O
HO
HO
Ans: 1. CH3)3SiCl / (CH3CH2)3N
2.
MgBr
3. H2O
4. TBAF
Topic: Protection of alcohols
Section: 13.7
Difficulty Level: Medium
89. Predict the structure of each product(A-D) for the following reaction sequence.
OH
O
1.
Br
(CH3)3SiCl
A
Mg/ ether
B
(CH3CH2)3N
C
2. H2O
Ans:
OSi(CH3)3
OSi(CH3)3
MgBr
Br
A
B
OH
OSi(CH3)3
HO
HO
D
C
Topic: Protection of alcohols
Section: 13.7
Difficulty Level: Medium
90. Predict the product for the following reaction sequence.
1.
OH
(CH3)3SiCl
Br
A)
B)
C)
D)
E)
2,4-heptanediol
1,4-heptanediol
2,5-octanediol
1,5-octanediol
none of these
Ans: B
Topic: Protection of alcohols
Section: 13.7
Difficulty Level: Medium
(CH3CH2)3N
Mg/ ether
H
O
H
2. H2O
TBAF
TBAF
D
91. Provide the reagents necessary to carry out the following conversion.
HO
HO
Ans: 1.
2.
3.
4.
(CH3)3SiCl / (CH3CH2)3N
NaNH2
CH3CH2CH2Br
TBAF
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Easy
92. Which of the following could be used to synthesize 1-bromopentane?
A)
B)
C)
D)
E)
CH3CH2CH2CH=CH2 +
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH=CH2 +
Ans: B
HBr 
+ PBr3 
+ NaBr 
+ Br2 
Br2 
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Easy
93. Provide the reagents necessary to convert 3-methyl-2-butanol to 2-bromo-3methylbutane.
A) conc. HBr
B) Br2
C) NaBr, H2SO4
D) PBr3
E) HBr, peroxide
Ans: D
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
94. Predict the product for the following reaction.
OH
PBr3
Br
Ans:
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Hard
95. Predict the major product for the following reaction and provide a curved arrow
mechanism for the formation of the product.
OH
HBr
Ans:
Br
Mechanism
OH
H
Br
OH2
+ Br
H
Br
Br
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Hard
+ H2O
96. Predict the major product for the following reaction.
OH
HCl
Ans:
Cl
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
97. Predict the product for the following reaction.
SOCl2/pyridine
OH
Ans:
Cl
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
98. Predict the major product for the following reaction.
H
OH
CH3
1. TsCl /pyridine
2. NaI
H
H
H
I
CH3
H
I
A)
B)
C)
D)
E)
II
H
I
H
OTs
H
Ts
CH3
CH3
CH3
III
H
IV
H
I
II
III
IV
both I and III
Ans: C
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
99. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine,
followed by sodium bromide.
A) trans-1-bromo-3-methylcyclopentane
B) cis-1-bromo-3-methylcyclopentane
C) 1-methylcyclopentene
D) 2-methylcyclopentene
E) 3-methylcyclopentene
Ans: A
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
100. The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene
goes via a(n) _____.
A) SN1 mechanism
B) SN2 mechanism
C) E1 mechanism
D) E2 mechanism
E) None of these.
Ans: C
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
101. Explain why the following reaction will not produce an alcohol as product.
Cl
OH
NaOH
not produced
Ans: The tertiary halide is too sterically hindered for an SN2 reaction with hydroxide as
nucleophile. Instead, the hydroxide ion is a strong base and will react with the
alkyl chloride to form alkene via an E2 mechanism.
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
102. Predict the major product for the following reaction.
OH
1. TsCl/pyridine
2. CH3CH2ONa
Ans:
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
103. Predict the major product for the following reaction.
OH
H2SO4

Ans:
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
104. Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane..
Ans: 1. H2SO4, heat
2. H2/Pd
OR
1. TsCl/pyridine
2. CH3CH2ONa
3. H2/Pd
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Medium
105. Provide a stepwise curved arrow mechanism for the following reaction.
HO
CH2CH3
CH2CH3
CH2CH3
CH2CH3
H2SO4

O
Ans:
H2O
HO
CH2CH3
CH2CH3
H
O
S
O
H
CH2CH3
O
CH2CH3
O
O
+
S
O
H
O
H
O
H3CH2C
H3CH2C
CH2CH3
H
O
CH2CH3
O
CH2CH3
CH2CH3
+ H2O
CH2CH3
+ H2SO4
CH2CH3
Topic: Reactions of Alcohols
Section: 13.9
Difficulty Level: Hard
S
O
106. Predict the product and provide a stepwise curved arrow mechanism for the following
reaction.
OH
OH
H2SO4
heat
Ans:
O
Mechanism
O
OH
H
O
S
O
H
OH2
OH
O
O
OH
+
O
S
O
H
O
O
H
O
OH
+ H2O
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Easy
H
O
S
O
O
H
O
+ H2SO4
107. Predict the product for the following reaction.
PCC
2-hexanol
CH2Cl2
O
A)
CH3COH
O
B)
CH3CH2CH2CH2COH
O
C)
CH3(CH2)3CCH3
O
D)
CH3CH2CH2CH2CH2COH
O
E)
CH3CH2CH2CH2CH2CH
Ans: C
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Medium
108. Provide the reagents necessary to carry out the following conversion.
OH
A)
B)
C)
D)
E)
KMnO4/NaOH/H2O
Na2Cr2O7/H2SO4/H2O
H2, Pt
Br2, CCl4
None of these
Ans: B
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Easy
O
109. Predict the product for the following reaction.
OH
Na2Cr2O7/H2SO4/H2O
O
Ans:
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Easy
110. Predict the product for the following reaction.
OH
PCC
CH2Cl2
H
Ans:
O
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Easy
111. Provide the reagents necessary to carry out the following conversion.
O
OH
A)
B)
C)
D)
E)
KMnO4/NaOH/H2O
Na2Cr2O7/H2SO4/H2O
PCC/CH2Cl2
Br2, CCl4
None of these
Ans: C
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Medium
H
112. Provide the reagents necessary to carry out the following conversion.
O
OH
A)
B)
C)
D)
E)
KMnO4/NaOH/H2O
Na2Cr2O7/H2SO4/H2O
PCC/CH2Cl2
Br2, CCl4
None of these
Ans: B
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Medium
113. Predict the product for the following reaction.
OH
excess
PCC/CH2Cl2
Ans:
CH2OH
OH
CH
O
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Medium
OH
114. Predict the product for the following reaction.
PCC
OH
CH2Cl2
Ans: No reaction. Tertiary alcohols do not undergo oxidation reactions.
Topic: Reactions of Alcohols
Section: 13.10
Difficulty Level: Medium
115. Predict the product for the following reaction.
PCC
cis-4-methylcyclohexanol
CH2Cl2
Ans:
O
.
Topic: Oxidation of Phenols
Section: 13.12
Difficulty Level: Medium
116. Predict the product for the following reaction.
OH
Na2Cr2O7/H2SO4/H2O
Ans:
O
O
Topic: Synthesis
.
Section: 13.13
Difficulty Level: Medium
117. Provide the structure for the final product (D), in the following reaction sequence.
O
CH3CH2CHOH
PBr3
Mg
A
ether
H3C
H
B
C
H2O
D
CH3
OH
Ans:
Topic: Synthesis
Section: 13.13
Difficulty Level: Medium
118. Provide the structure for each product (A-C) in the following reaction sequence.
1. O
CH3CH2CHOH
PBr3
Mg
A
ether
CH3
H3C
B
H
C
2. H2O
OH
Ans:
Br
A
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
MgBr
B
C
119. Provide the structure for the final product (E), in the following reaction sequence.
O
PBr3
OH
Mg
A
B
H
H2O
H
ether
PCC
E
D
C
CH2Cl2
OH
O
H
OH
II
I
III
A)
B)
C)
D)
E)
V
IV O
O
I
II
III
IV
V
Ans: C
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
120. Provide the structure for each product (A-D) in the following reaction sequence.
1.
PBr3
OH
Mg
A
B
ether
O
H
PCC
H
D
C
2. H2O
CH2Cl2
Ans:
O
OH
Br
A
Topic: Synthesis
Section: 13.13
Difficulty Level: Medium
MgBr
B
C
D
121. Provide the structure for product (A), in the following reaction sequence.
OH
PBr3
Mg
D2O
A
ether
A)
B)
C)
D)
E)
CH3CH2CH2CH3
CH3CH2CHDCH3
CH3CH2CHODCH3
CH3CH2CH2CH2OD
CH3CH2CH2CH2D
Ans: B
Topic: Synthesis
Section: 13.13
Difficulty Level: Medium
122. Provide the reagents necessary to carry out the following conversion.
O
OH
Ans: 1. PBr3
2. Mg/ether
O
H
3.
4. H2O
5. PCC/CH2Cl2
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
123. Provide a stepwise synthesis for the following.
Cl
Ans:
Cl2
OH
H3O+
CH3CH2ONa
PCC
h
CH2Cl2
O
OH
H2SO4
1. CH3MgBr
2. H2O
heat
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
124. Provide the product for the following reaction sequence:
MgBr
MgBr
OH
PCC
CH2Cl2
I
O
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: C
ether
ether
O
OH
H2O
K2Cr2O7/H2SO4/H2O
H2O
HO
III
II
V
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
125. Predict the product, for the following reaction sequence,
O
3,4-dimethyl-1-hexanol
SOCl2
Mg/ether
pyridine
1.
H
CrO3/ H2SO4/H2O
2. H3O+
O
OH
III
II
I
OH
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: B
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
O
OH
H
V
O
126. Provide a stepwise synthesis for the following.
O
Ans:
Cl
OH
CH3CH2ONa
Br2
h
1. BH3 THF
PCC
2. H2O2/NaOH/H2O
CH2Cl2
O
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
127. Provide the reagents necessary to carry out the following conversion.
O
O
Ans: 1.
2.
3.
4.
Cl2/h
CCONa
KMnO4/NaOH/H2O
excess PCC/CH2Cl2
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
128. Provide the reagents necessary to carry out the following conversion.
O
HO
Ans: 1. (CH3)3SiCl/ (CH3CH2)3N
2. CH3MgBr
3. H3O+
Topic: Synthesis
HO
HO
Section: 13.13
Difficulty Level: Medium
129. Provide the reagents necessary to carry out the following conversion.
O
OH
Br
Ans: 1. NaOH
2. Na2Cr2O7/H2SO4/H2O
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
130. Provide a stepwise synthesis to carry out the following conversion.
Ans:
Br
Br2
CH3CH2ONa
2. H2O2/NaOH/H2O
CH3
PCC
CH2Cl2
H2/Pd
Topic: Synthesis
Section: 13.13
Difficulty Level: Hard
1. BH3 THF
OH
h
O
1. CH3MgBr
2. H2O
H2SO4
OH
heat
131. Provide a stepwise synthesis to carry out the following conversion.
O
OH
OH
Ans:
OH
PBr3
Br
Mg/ether
MgBr
O
1. O
H
H
OH
2. H2O
CrO3/H2SO4/H2O
OH
Topic: Spectroscopy
Section: 13 & 15.6
Difficulty Level: Medium
132. Which one of the following compounds is consistent with the following IR spectrum?
SDBS: National Institute of Advanced Industrial Science and Technology
OH
I
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: A
Topic: Spectroscopy
Section: 13 & 15.6
Difficulty Level: Medium
OH
OH
C
II
N
III
O
HO
C
IV
N
133. Which one of the following compounds is consistent with the following IR spectrum?
SDBS: National Institute of Advanced Industrial Science and Technology
OH
OH
I
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: E
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
Difficulty Level: Hard
II
OH
O
O
OH
OH
III
IV
V
134. Which of the following compounds is consistent with the following proton decoupled
13
C NMR spectrum?
80
70
60
50
40
PPM
OH
OH
30
20
OH
HO
I
A)
B)
C)
D)
E)
I
II
III
IV
none of these
Ans: B
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
Difficulty Level: Hard
II
III
IV
10
0
135. Which of the following compounds is consistent with the following proton decoupled
13
C NMR spectrum?
70
60
50
40
PPM
30
20
10
OH
OH
HO
I
A)
B)
C)
D)
E)
I
II
III
IV
none of these
Ans: A
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
Difficulty Level: Hard
II
III
IV
OH
0
136. A compound with a molecular formula C9H12O has the following 1HNMR spectrum.
Which of the following structures is consistent with this spectrum?
3
2
2
2
2
1
exchanges with D2O
7
6
O
I
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: C
Topic: Spectroscopy
Section: 13, 16.11 & 16.12
Difficulty Level: Hard
5
4
PPM
3
1
OH
OH
II
2
III OH
IV
0
OH
V
137. A compound with a molecular formula C6H14O displays the following 1HNMR and
13
CNMR spectra. Propose astructure for this compound.
9
3
2
90
80
70
60
50
40
PPM
Ans:
OH
30
1
20
10
0