Chapter 8 Alcohols, Ethers, and Thiols
Multiple Choice
1. Which is the IUPAC name for the following structure? (Sec. 8.2)
OH
a)
b)
c)
d)
cyclohexenol
3-cyclohexen-1-ol
1-cyclohexen-4-ol
4-cyclohexenol
2. Which structures have the correct IUPAC name? (Sec. 8.2)
CH2OH
O
C OCH
H
3
H3C
O
CH2
cis-1,2-dimethoxycyclohexane
I
R-2-methoxy-1-propanol
II
OH
H3C
HC OCH3
H3C
OH
2-methoxypropane
III
a)
b)
c)
d)
trans-1,3-cyclohexanediol
IV
I, II
III, IV
II, III
I, IV
3. Arrange the compounds in the order of increasing solubility in water (least first). (Sec. 8.4)
CH3CH2CH2CH2OCH3
I
CH3OCH2CH2OCH3
III
a)
b)
c)
d)
CH3OCH3
II
CH3CH2CH2CH2CH2OH
IV
I, III, II, IV
III, I, IV, II
I, IV, II, III
IV, I, III, II
88
Chapter 8 Alcohols, Ethers, and Thiols
4. Which are secondary alcohols? (Sec. 8.2)
CH3
CH3
H3C
OH
C C
H3C C OH
OH
H
H
H
CH3
CHCH3
OH
I
a)
b)
c)
d)
II
III
IV
I, III
II, III
III, IV
I, IV
5. Arrange the compounds in the order of increasing acidity (least first). (Sec. 8.3)
CH3
CH3CH2OH
I
a)
b)
c)
d)
CH3COH
CH3
II
OH
CH3CHCH3
H2O
III
IV
III, I, II, IV
I, III, IV, II
II, III, I, IV
II, I, III, IV
6. Arrange the compounds in the order of increasing acidity (least first). (Sec. 8.6)
H3C
CHOH
CH3CH2SH
H2S
H2O
II
III
IV
H3C
I
a)
b)
c)
d)
II, I, III, IV
I, IV, II, III
III, II, I, IV
II, I, IV, III
89
Chapter 8 Alcohols, Ethers, and Thiols
7. Arrange the compounds in the order of increasing boiling point (lowest first). (Sec. 8.3, 8.4, 8.6)
H3C
O
CH3
I
a)
b)
c)
d)
H2O
CH3CH2OH
CH3CH2SH
II
III
IV
II, I, III, IV
I, IV, II, III
IV, I, III, II
I, IV, III, II
8. Arrange the compounds in the order of increasing solubility in water (lowest first). (Sec. 8.2)
CH3OH
CH3CH2CH2CH2CH2OH
I
II
CH3CH2CH2CH2OH
HOCH2CH2CH2CH2CH2OH
III
IV
a)
b)
c)
d)
IV, III, II, I
II, III, IV, I
III, IV, II, I
II, IV, III, I
9. Which alcohol will form the most stable carbocation? (Sec. 8.3)
CH3
a)
CH3CHCH2OH
CH3
b)
CH3
COH
CH3
c)
d)
OH
CH3OH
90
Chapter 8 Alcohols, Ethers, and Thiols
10. How many isomers, including stereoisomers, can be formed from the hydroxylation of 4methylcyclohexene using osmium tetroxide? (Sec. 8.3, 8.4)
a)
b)
c)
d)
2
4
6
8
11. Arrange the following in order of increasing ability to hydrogen bond (lowest first). (Sec. 8.3, 8.4, 8.6)
I.
III.
a)
b)
c)
d)
CH3
II.
H
CH3O H
CH3S
H
IV. HO H
I, II, III, IV
III, I, IV, II
II, IV, I, III
I, IV, II, III
12. Which reagents do not effect the following conversion? (Sec. 8.3)
HO
a)
b)
c)
d)
CH3
Cl
CH3
HCl
Cl2
SOCl2
NaCl
I.
II.
III.
IV.
I, II
II, III
II, IV
I, III
13. Which is the major product from the acid catalyzed hydrolysis of cyclohexene oxide? (Sec. 8.5)
a)
b)
H H
OH H
H OH
HO OH
O
c)
d)
91
Chapter 8 Alcohols, Ethers, and Thiols
14. Which is the major product of the following reaction? (Sec. 8.5)
H
2
H
H
C C
+
H
O
H2NCH2CH2NH2
a) HOCH2CH2NH2
b) O
N
c) HOCH2CH2NHCH2CH2OH
d) HOCH2CH2NHCH2CH2NHCH2CH2OH
15. Which is the best method for making the following conversion? (Sec. 8.3)
OH
CH3CH2CH2OH
a)
H3PO4
heat
CH3CHCH3
dilute
H2SO4
Pt / H2
b)
dilute
H2SO4
O
c)
PCC
d)
COO H
H3PO4
heat
16. Which is the product of the following reaction? (Sec. 8.3, 8.5)
OH
H3PO4
heat
OsO4 / ROOH
OH
a)
O
b)
OH
OH
H
O
c)
O
d)
H
92
Chapter 8 Alcohols, Ethers, and Thiols
17. Which is the product of the following reaction? (Sec. 8.3)
CH2OH
PCC
O
O
O
H
b)
a)
O
O
C
c) H3CCCH2CH2CH2CH
d)
18. Treatment of cyclopentene with dilute sulfuric acid, followed by reaction with chromic acid gives
which of the following compounds as the major product? (Sec. 8.3)
O
OH
O
a)
b)
OH
c)
O
d)
O
19. Which is the major product of the following reaction? (Sec. 8.3, 8.5)
CH3
Pt / H2
H3PO4
CH3CHCH2OH
heat
CH3
CH3
a) CH3CHCH
b) CH3CHCOH
O
O
CH3
c) CH3CHCH3
d) CH3CH2CH2CH3
20. Which are the best conditions for the preparation of 1-chloro-2-methylpropane starting from 2-methyl1-propanol? (Sec. 8.3)
a)
c)
H3PO4
HCl
heat
K
Cl2
b)
d)
SOCl2
NaCl
93
OH
Chapter 8 Alcohols, Ethers, and Thiols
21. Which is the major product of the following reaction? (Sec. 8.5)
H3C
O
COOH
CH2Cl2
HO CH3 OH H3C O
a)
b)
HO CH2
H3C O
c)
d)
22. Which is the major product of the following reaction? (Sec. 8.3, 8.5)
O
C C
H
H
+
H / H2O
H
O O
a)
CrO3
H2SO4
O O
C COH
b)
C CH
O
c)
OH O
C CH2OH
d)
23. Arrange the following in order of increasing rate of reactivity with HBr (least first). (Sec. 8.3)
OH
OH
CH2OH
CH3
I
a)
b)
c)
d)
CH3OH
II
III
I, II, IV, III
II, I, III, IV
IV, III, I, II
III, II, IV, I
24. Classify the following reaction. (Sec. 8.6)
CH3CH2S
a)
b)
c)
d)
SCH2CH3
2 CH3CH2SH
oxidation
reduction
neither
both
94
IV
CH COH
Chapter 8 Alcohols, Ethers, and Thiols
25. Which is the major product of the following reaction? (Sec. 8.5)
O
+
H / H2O
C CH CH2CH3
H3C
H3C
a)
b)
c)
d)
3-pentanol
2-pentanol
2-methyl-2,3-pentanediol
4-methyl-3,4-pentanediol
Fill in the Blank
1. The major product of the following reaction is,
OH
H2SO4
heat
(Sec. 8.3)
2. The major product of the following reaction is,
H2CrO4
OH
acetone
H2O
(Sec. 8.3)
3. The major product of the following reaction is,
Na
OH
(Sec. 8.3)
4. The major product of the following reaction is,
H2NCH3
O
(Sec. 8.5)
5. The reagent needed to complete the following reaction is,
O
OH
95
(Sec. 8.3)
Chapter 8 Alcohols, Ethers, and Thiols
6. The reagent needed to complete the following reaction is,
Cl
OH
(Sec. 8.3)
7. The reagent needed to complete the following reaction is,
O
(Sec. 8.5)
8. The starting material needed to complete the following reaction is,
H3PO4
heat
(Sec. 8.3)
9. The starting material needed to complete the following reaction is,
SOCl2
Cl
(Sec. 8.3)
10. The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,
H
OH
H SO4H
O
H
H
+
H
-
(Sec. 8.3)
96
SO4H
C
+
H
H
Chapter 8 Alcohols, Ethers, and Thiols
True-False
1. The strongest acid in the following list is water. (Sec. 8.3, 8.4, 8.6)
H3C
O
S
H3C
CH3
CH3
O
H
H
H3C
O
S
H H3C
H
2. The major product of the reaction of 1-propanol with PCC is propanoic acid. (Sec. 8.3)
3. The product of the reaction of methanol with sodium metal is sodium methoxide. (Sec. 8.3)
4. The major product of the reaction of 3-methyl-2-butanol with hot, concentrated sulfuric acid is 3methyl-1-butene. (Sec. 8.3)
5. The following compound is named 1-chloro-2,2-dimethyl-4-pentanol. (Sec. 8.2)
Cl
OH
6. The following compound is named 2,6-dimethyl-1,4-cyclohexanediol. (Sec. 8.2)
OH
OH
7. The following compounds are listed in decreasing boiling point order (highest first). (Sec. 8.2)
H3C
O
H > CH CH
3
2
O
H > CH3CH2CH2
O
H > CH3CH2CH2CH2
O
H
8. The following compounds are listed in decreasing boiling point order (highest first). (Sec. 8.2, 8.4)
H3C
O
CH3 > H3C
O
H >
H
O
H
9. The following compounds are listed in decreasing order of solubility in water (highest first). (Sec. 8.2)
CH3CH2CH2CH2
O
H > CH3CH2CH2
O
H > CH3CH2
O
H > H3C
10. The following compounds are listed in increasing order of solubility in water (lowest first).
(Sec. 8.2, 8.4)
<
OH
<
97
O
O
H
Chapter 8 Alcohols, Ethers, and Thiols
Answers
Multiple Choice
1. b
2. b
3. c
4. c
5. c
6. b
7. d
8. b
9. b
10. a
11. a
12. c
13. b
14. d
15. a
16. a
17. b
18. c
19. c
20. b
21. d
22. a
23. c
24. b
25. c
Fill in the Blank
1.
2.
OH
O
3.
O
Na+
4.
OH
NHCH3
5. PCC
98
Chapter 8 Alcohols, Ethers, and Thiols
6. SOCl2
7. a peracid
8.
OH
9.
OH
10.
H
OH
H SO4 H
O
H
H
+
H
-
True-False
1. F
2. F
3. T
4. F
5. F
6. T
7. F
8. F
9. F
10. F
99
SO4 H
C
+
H
H