Chapter 8 - Alcohols, Ethers, and Thiols
Multiple Choice
Section: 8.1
Difficulty Level: Easy
1. Which is the IUPAC name for the following structure?
OH
a)
b)
c)
d)
cyclohexenol
3-cyclohexen-1-ol
1-cyclohexen-4-ol
4-cyclohexenol
Section: 8.1
Difficulty Level: Easy
2. Arrange the compounds in the order of increasing solubility in water (least soluble first). (help: add the
lone pairs to the oxygen atoms and look for the possibility of hydrogen bonding between the molecules and
water)
OH
I
a)
b)
c)
d)
OH
OH
OH
HO
II
III
IV
I, III, II, IV
III, I, IV, II
I, IV, II, III
IV, I, III, II
Section: 8.1
Difficulty Level: Hard
3. Arrange the compounds in the order of increasing solubility in water (least soluble first). (help: estimate
the hydrophobic surface of the non-polar part of the molecules)
OH
OH
OH
I
II
a)
b)
c)
d)
OH
III
IV
III, IV, II, I
II, III, IV, I
IV, III, II, I
III, IV, I, II
140
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.1
Difficulty Level: Hard
4. Arrange the compounds in the order of increasing solubility in water (least soluble first). (help: estimate
the hydrophobic surface of the non-polar part of the molecules)
OH
OH
I
II
OH
OH
III
a)
b)
c)
d)
IV
II, III, I, IV
I, II, III, IV
IV, II, III, I
II, IV, III, I
Section: 8.2
Difficulty Level: Easy
5. Arrange the compounds in the order of increasing acidity (least first).
OH
OH
I
II
a)
b)
c)
d)
OH
III
III, I, II, IV
I, III, IV, II
II, III, I, IV
II, I, III, IV
141
H2O
IV
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Easy
6. Which alcohol will form the most stable carbocation?
OH
OH
I
a)
b)
c)
d)
OH
II
III
OH
IV
I
II
III
IV
Section: 8.2
Difficulty Level: Easy
7. Which are the best conditions for the preparation of 1-chloro-2-methylpropane starting from 2-methyl-1propanol?
a)
c)
a)
b)
c)
d)
H3PO4
HCl
heat
K
Cl2
b)
d)
SOCl2
NaCl
a
b
c
d
142
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Easy
8. Arrange the following in order of increasing rate of reactivity with HBr (least first).
OH
OH
CH2OH
CH3
I
a)
b)
c)
d)
CH3OH
II
IV
III
I, II, IV, III
II, I, III, IV
IV, III, I, II
III, II, IV, I
Section: 8.2
Difficulty Level: Medium
9. Which molecules are secondary alcohols?
OH
OH
OH
HO
I
II
a)
b)
c)
d)
III
I, III
II, III
III, IV
I, IV
143
IV
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
10. 2-(1-hydroxypropan-2-yl)cyclopentanol reacts with a mixture of potassium dichromate in
concentrated sulfuric acid at room temperature. What product is formed? (help: assume that you
have sufficient quantities of oxidizer to perform all possible reactions.)
HO
K2Cr2O7/H2SO3
HO
HO
O
HO
HO
I
II
O
O
O
III
O
H
a)
b)
c)
d)
IV
HO
O
I
II
III
IV
144
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
11. 2-(1-hydroxypropan-2-yl)cyclopentanol reacts with pyridinium chlorochromate in dioxane
under reflux. What product is formed? (help: assume that you have sufficient quantities of
oxidizer to perform all possible reactions.)
HO
K2Cr2O7/H2SO3
HO
HO
O
HO
HO
I
II
O
O
O
III
O
H
a)
b)
c)
d)
IV
HO
O
I
II
III
IV
145
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
12. The alcohol shown below reacts with thionyl chloride in pyridine. Which organic product is formed?
O
SOCl2
pyridine
HO
O
O
Cl
Cl
HO
I
II
O
ClOS
O
O
III
a)
b)
c)
d)
IV
I
II
III
IV
146
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
13. Which reagents do not effect the following conversion?
HO
a)
b)
c)
d)
CH3
Cl
CH3
HCl
Cl2
SOCl2
NaCl
I.
II.
III.
IV.
I, II
II, III
II, IV
I, III
Section: 8.2
Difficulty Level: Medium
14. Which is the best method for making the following conversion?
OH
CH3CH2CH2OH
H3PO4
a)
heat
CH3CHCH3
dilute
H2SO4
b)
Pt / H2
dilute
H2SO4
O
PCC
c)
a)
b)
c)
d)
d)
H3PO4
heat
a
b
c
d
147
COO H
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
15. Which is the product of the following reaction?
PCC
OH
O
dioxane
HO
H
OH
O
HO
II
I
O
H
H
O
III
a)
b)
c)
d)
IV
I
II
III
IV
148
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
16. Which is the product of the following reaction?
OH
H3PO4
heat
OH
OH
O
OH
O
OH
II
I
a)
b)
c)
d)
IV
III
I
II
III
IV
Section: 8.2
Difficulty Level: Medium
17. Which is the major product of the following reaction?
CH3
CH3CHCH2OH
Pt / H2
H3PO4
heat
CH3
a) CH3CHCH
O
CH3
b) CH3CHCOH
O
CH3
c) CH3CHCH3
a)
b)
c)
d)
d) CH3CH2CH2CH3
a
b
c
d
149
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Hard
18. 4-(2-hydroxyethyl)-1-methylcyclohexanol reacts with HBr (gas) in diethyl ether at 5 oC. What is the
main product formed?
HBr
OH
HO
OH
Br
diethyl ether
Br
HO
II
I
HO
HO
III
a)
b)
c)
d)
IV
I
II
III
IV
150
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Hard
19. 4-(2-hydroxyethyl)-1-methylcyclohexanol reacts with HBr (gas) in dioxane under pressure at 125oC.
What is the main product formed?
HBr
dioxane
OH
HO
OH
Br
Br
Br
II
I
Br
Br
III
a)
b)
c)
d)
IV
I
II
III
IV
151
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Hard
20. Which of the molecules are primary alcohols?
HO
OH
geraniol
farnesol
II
I
H
S
HN
O
OH
H
O
N H
H
H
HO
biotin
cholesterol
III
a)
b)
c)
d)
H
IV
III, II
IV, I
II, III
I, II
Section: 8.3
Difficulty Level: Medium
21. Which is the major product of the following reaction?
H3C
O
COOH
CH2Cl2
HO CH3 OH H3C O
a)
b)
HO CH2
H3C O
c)
d)
a) a
b) b
c) c
d) d
152
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.1 and 8.3
Difficulty Level: Medium
22. Which structures have the correct IUPAC name?
CH2OH
O
O
CH2
cis-1,2-dimethoxycyclohexane
I
C OCH
H
3
H3C
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
153
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.4
Difficulty Level: Medium
23. Which is the major product from the acid catalyzed hydrolysis of cyclohexene oxide?
a)
b)
H H
OH H
H OH
HO OH
O
d)
c)
a)
b)
c)
d)
a
b
c
d
Section: 8.4
Difficulty Level: Hard
24. Which is the major product of the following reaction?
O
H2S
a) 2-mercapto-2-methyl-3-pentanol
b) 3-mercapto-2-methyl-2-pentanol
c) 2-methyl-2,3-pentanediol
d) 4-methyl-3,4-pentanediol
154
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.4
Difficulty Level: Hard
25. The alkene shown below reacts with meta-chloroperbenzoic acid (MCPBA) in tetrahydrofuran. Which
of the four formulas correctly describe the reaction products?
O
O
H
O O
(MCPBA)
Cl
THF
O
O
O
O
I
O
II
O
O
III
IV
HO
HO
a)
b)
c)
d)
III
II
I
IV
155
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2, 8.3, and 8.4
Difficulty Level: Hard
26. Which is the product of the following reaction?
OH
H3PO4
RCO3H
CH3
OH
heat
H
OH
O
H
a)
b)
c)
d)
H
OH
O CH3
O CH3
H
II
I
H
H
IV
III
I
II
III
IV
Section: 8.2 and 8.4
Difficulty Level: Medium
27. Which is the major product of the following reaction?
O
C
H
C
H
H
O O
a)
C
a)
b)
c)
d)
+
H / H2O
COH
CrO3
H2SO4
O O
b)
C
CH
a
b
c
d
156
O
c)
C
OH O
CH2OH
d)
CH COH
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.3 and 8.4
Difficulty Level: Medium
28. Which is the major product of the following reaction?
H
2
H
H
C C
+
H
O
a) HOCH2CH2NH2
H2NCH2CH2NH2
b) O
c) HOCH2CH2NHCH2CH2OH
a)
b)
c)
d)
N
d) HOCH2CH2NHCH2CH2NHCH2CH2OH
a
b
c
d
Section: 8.1 and 8.5
Difficulty Level: Easy
29. Arrange the compounds in the order of increasing boiling point (lowest first). (help: add the lone pairs
to the oxygen/sulfur atoms and look for the possibility of hydrogen bonding between the molecules and
water)
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
157
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2 and 8.5
Difficulty Level: Easy
30. Arrange the following in order of increasing ability to hydrogen bond (lowest first).
I.
III.
a)
b)
c)
d)
CH3
H
CH3O H
II.
CH3S
H
IV. HO H
I, II, III, IV
III, I, IV, II
II, IV, I, III
I, IV, II, III
Section: 8.6
Difficulty Level: Easy
31. Arrange the compounds in the order of increasing acidity (least first).
OH
I
SH
H2S
H2O
III
IV
II
a)
b)
c)
d)
II, I, III, IV
I, IV, II, III
III, II, I, IV
II, I, IV, III
Section: 8.6
Difficulty Level: Easy
32. Classify the following transformation of a disulfide to two sulfides. How can that transformation be
brought about?
CH3CH2S
a)
b)
c)
d)
SCH2CH3
2 CH3CH2SH
oxidation
reduction
neither
both
158
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.6
Difficulty Level: Medium
33. Arrange the compounds in the order of increasing acidity (least acidic first).
F
SH
SH
II
I
SH
SH
Br
III
a)
b)
c)
d)
IV
II, III, IV, I
I, III, IV, II
III, IV, II, I
IV, II, III, I
159
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.6
Difficulty Level: Medium
34. Classify the following reaction:
O
O
NH2 O
HO
NH
HO
HN
O
O
S
S
O
NH
OH
HN
HO
O
glutathione disulfide
NH2 O
O
HO
HN
2
HS
O
OH
HN
O
NH2 O
glutathione
a)
b)
c)
d)
oxidation
reduction
neither
both
160
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2 and 8.6
Difficulty Level: Medium
35. Arrange the compounds in the order of increasing acidity (least acidic first).
SH
NH2
I
II
a)
b)
c)
d)
H2S
OH
III
IV
II, IV, I, III
III, IV, I, II
IV, III, II, I
I, III, IV, II
Fill in the Blank Questions
Section: 8.2
Difficulty Level: Easy
1. The major product of the following reaction is,
Na
+ 1/2 H2
OH
Section: 8.2
Difficulty Level: Easy
2. The reagent needed to complete the following reaction is,
H
OH
O
Section: 8.2
Difficulty Level: Easy
3. The reagent needed to complete the following reaction is,
Cl
OH
161
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
4. The major product of the following reaction is,
OH
H2SO4
heat
Section: 8.2
Difficulty Level: Medium
5. The major product of the following reaction is,
H2CrO4
OH
acetone
H2O
Section: 8.2
Difficulty Level: Medium
6. The starting material needed to complete the following reaction is,
H3PO4
heat
Section: 8.2
Difficulty Level: Medium
7. The starting material needed to complete the following reaction is,
SOCl2
Cl
162
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Hard
8. The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,
H
OH
O
O
H
O
O
O
S
OH
S
H
H
OH
O
O
+ H2SO4
+ H2 O
Section: 8.4
Difficulty Level: Easy
9. The reagent needed to complete the following reaction is,
O
Section: 8.4
Difficulty Level: Medium
10. The major product of the following reaction is,
H2NCH3
O
163
Chapter 8 - Alcohols, Ethers, and Thiols
True-False Questions
Section: 8.1
Difficulty Level: Easy
1. The following compounds are listed in decreasing order of solubility in water (highest first).
CH3CH2CH2CH2
O
H > CH3CH2CH2
O
H > CH3CH2
O
H > H3C
O
H
Section: 8.1
Difficulty Level: Medium
2. The following compound is named 1-chloro-2,2-dimethyl-4-pentanol.
Cl
OH
Section: 8.1
Difficulty Level: Medium
3. The following compound is named 2,6-dimethyl-1,4-cyclohexanediol.
OH
OH
Section: 8.1
Difficulty Level: Medium
4. The following compounds are listed in decreasing boiling point order (highest first).
H3C
O
H > CH CH
3
2
O
H > CH3CH2CH2
O
H > CH3CH2CH2CH2
Section: 8.2
Difficulty Level: Easy
5. The major product of the reaction of 1-propanol with PCC is propanoic acid.
164
O
H
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Easy
6. The product of the reaction of methanol with sodium metal is sodium methoxide.
Section: 8.2
Difficulty Level: Medium
7. The major product of the reaction of 3-methyl-2-butanol with hot, concentrated sulfuric acid is 3methyl-1-butene.
Section: 8.1 and 8.3
Difficulty Level: Easy
8. The following compounds are listed in decreasing boiling point order (highest first).
H3C
O
CH3 > H3C
O
H >
H
O
H
Section: 8.1 and 8.3
Difficulty Level: Medium
9. The following compounds are listed in increasing order of solubility in water (lowest first).
OH
<
<
O
Section: 8.2, 8.3, and 8.6
Difficulty Level: Easy
10. The strongest acid in the following list is water.
H3C
O
CH3
H3C
S
CH3
H
O
H
165
H3C
O
H H3C
S
H
Chapter 8 - Alcohols, Ethers, and Thiols
Answers
Multiple Choice
1. b
2. c
3. c
solubilities in water: cyclohexanol: 42g/L; cyclopentanol: 97g/L, cyclopentenol: 124g/L, cyclobutanol:
154g/L
4. b
solubilities in water: pentanol: 20g/L, 1-methyl-1-butanol: 28g/L, 2-methyl-1-butanol: 30g/L, 2,2-dimethyl1-propanol: 42g/L
5. c
6. b
7. b
8. c
9. c
10. d
11. c
12. a
13. c
14. a
15. c
16. c
17. c
18. b
19. d
20. d
21. d
22. b
23. b
24. b
25. c
26. d
27. a
28. d
29. d
30. a
31. b
32. b
33. b
34. b
35. a
Fill in the Blank Questions
1.
O
Na
2. PCC
3. SOCl2
166
Chapter 8 - Alcohols, Ethers, and Thiols
4.
5.
OH
O
6.
OH
7.
OH
8.
H
O
OH
O
H
O
O
O
S
S
H
H
OH
O
OH
O
+ H2SO4
+ H2O
9. a peracid
167
Chapter 8 - Alcohols, Ethers, and Thiols
10.
OH
NHCH3
True-False Questions
1. F
2. F
3. T
4. T
5. F
6. T
7. F
8. F
9. F
10. F
168