Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.1
Difficulty Level: Easy
1. Which is the IUPAC name for the following structure?
OH a) cyclohexenol b) 3-cyclohexen-1-ol c) 1-cyclohexen-4-ol d) 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
OH OH
HO
OH
I II III IV a) I, III, II, IV b) III, I, IV, II c) I, IV, II, III d) 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 OH
I II a) III, IV, II, I b) II, III, IV, I c) IV, III, II, I d) III, IV, I, II
III IV
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 IV a) II, III, I, IV b) I, II, III, IV c) IV, II, III, I d) II, IV, III, I
Section: 8.2
Difficulty Level: Easy
5. Arrange the compounds in the order of increasing acidity (least first).
OH
OH OH H
2
O
II III IV I a) III, I, II, IV b) I, III, IV, II c) II, III, I, IV d) II, I, III, IV
141

Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Easy
6. Which alcohol will form the most stable carbocation?
OH OH OH OH
I II III IV a) I b) II c) III d) 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)
H
3
PO
4 heat
HCl b)
SOCl
2 c) a) a b) b c) c d) d
K Cl
2 d)
NaCl
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
CH
2
OH
CH
3
CH
3
OH
III IV I II a) I, II, IV, III b) II, I, III, IV c) IV, III, I, II d) III, II, IV, I
Section: 8.2
Difficulty Level: Medium
9. Which molecules are secondary alcohols?
OH
OH
OH
I II
HO
III IV a) I, III b) II, III c) III, IV d) I, IV
143

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
K
2
Cr
2
O
7
/H
2
SO
3
HO
HO
O
HO
I
O
HO
O
II
O
O
H
III a) I b) II c) III d) IV
HO
O
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
K
2
Cr
2
O
7
/H
2
SO
3
HO
HO
O
HO
I
O
HO
O
II
O
O III
H a) I b) II c) III d) IV
HO
O
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
SOCl
2 pyridine
HO
O
O
Cl
Cl
HO
I
O
II
O
ClOS a) I b) II c) III d) IV
III
O
IV
146

Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
13. Which reagents do not effect the following conversion?
HO CH
3
CH
3
CH
2
CH
2
OH
Cl
HCl Cl
2
SOCl
2
I.
II.
III.
a) I, II b) II, III c) II, IV d) I, III
Section: 8.2
Difficulty Level: Medium
14. Which is the best method for making the following conversion?
NaCl
IV.
OH
CH
3
CHCH
3
CH
3 a)
H
3
PO
4 heat dilute
H
2
SO
4 b)
Pt / H
2 dilute
O
H
2
SO
4
COO H c)
PCC d)
H
3
PO
4 heat a) a b) b c) c d) d
147

Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
15. Which is the product of the following reaction?
OH
PCC dioxane
I
OH
O HO
HO
H
III a) I b) II c) III d) IV
O
H
O
II
H
IV
O
148

Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
16. Which is the product of the following reaction?
OH
H
3
PO
4 heat
OH
OH
O
OH
O
OH
I II
III IV a) I b) II c) III d) IV
Section: 8.2
Difficulty Level: Medium
17. Which is the major product of the following reaction?
CH
3
CH
3
CHCH
2
OH
H
3
PO
4
Pt / H
2 heat
CH
3 a) CH
3
CHCH
O
CH
3 b) CH
3
CHCOH
O c)
CH
3
CH
3
CHCH
3 d) CH
3
CH
2
CH
2
CH
3 a) a b) b c) c d) 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 o C. What is the main product formed?
HBr
OH
HO diethyl ether
II
Br
Br
HO a) I b) II c) III d) IV
III
I
OH
HO
HO
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 125 o C.
What is the main product formed?
HBr
OH dioxane
HO
II
Br
Br
Br a) I b) II c) III d) IV
III
I
OH
Br
Br
IV
151

Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Hard
20. Which of the molecules are primary alcohols?
HO
OH farnesol
I geraniol
II
HN
H
S
OH
O N
H
H
O biotin
HO
III a) III, II b) IV, I c) II, III d) I, II
Section: 8.3
Difficulty Level: Medium
21. Which is the major product of the following reaction?
H
H
3
C
O
COOH
H
IV
H cholesterol
CH
2
Cl
2
HO CH
3
OH H
3
C O HO CH
2
H
3
C O a) b) 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?
CH
2
OH
O O
CH
2
H
H
3
C
C
OCH
3 cis-1,2-dimethoxycyclohexane
I
R-2-methoxy-1-propanol
II
OH
H
3
C
H C
H
3
C
OCH
3
OH
2-methoxypropane
III a) I, II b) III, IV c) II, III d) I, IV trans-1,3-cyclohexanediol
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) H H b)
OH
H
HO OH
H
OH
O c) d) a) a b) b c) c d) d
Section: 8.4
Difficulty Level: Hard
24. Which is the major product of the following reaction?
O
H
2
S 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
O O
H
(MCPBA)
Cl
THF
O O
O
I
O
O
O
O
II
HO
HO a) III b) II c) I d) IV
III
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
H
3
PO
4
RCO
3
H CH
3
OH heat
H
H
O
OH
H
H
O CH
3
I II
III a) I b) II c) III d) IV
Section: 8.2 and 8.4
Difficulty Level: Medium
27. Which is the major product of the following reaction?
O
H
C C
H
H
H
+
/ H
2
O CrO
3
H
2
SO
4
O O O O a) C COH b) C CH c) a) a b) b c) c d) d
IV
H
OH
H
O CH
3
O
C CH
2
OH d)
OH O
CH COH
156

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 H
2 C C +
H
O
H a) HOCH
2
CH
2
NH
2
H
2
NCH b)
2
CH
O
2
NH
2
N c) HOCH
2
CH
2
NHCH
2
CH
2
OH d) HOCH
2
CH
2
NHCH
2
CH
2
NHCH
2
CH
2
OH a) a b) b c) c d) 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)
H
3
C
O
CH
3
H
2
O CH
3
CH
2
OH CH
3
CH
2
SH
I II III IV a) II, I, III, IV b) I, IV, II, III c) IV, I, III, II d) 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.
CH
3
H II.
CH
3
S H
III.
CH
3
O H IV.
HO H a) I, II, III, IV b) III, I, IV, II c) II, IV, I, III d) I, IV, II, III
Section: 8.6
Difficulty Level: Easy
31. Arrange the compounds in the order of increasing acidity (least first).
OH SH
H
2
S
H
2
O
I II III IV a) II, I, III, IV b) I, IV, II, III c) III, II, I, IV d) 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?
CH
3
CH
2
S SCH
2
CH
3
2 CH
3
CH
2
SH a) oxidation b) reduction c) neither d) 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
I II
SH
SH
III a) II, III, IV, I b) I, III, IV, II c) III, IV, II, I d) IV, II, III, I
Br
IV
159

Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.6
Difficulty Level: Medium
34. Classify the following reaction:
O
HO
NH
2 O
O
HO
O
O
HO
NH
HN
S S
NH
HN glutathione disulfide
O
O
O
HO
OH
NH
2
O
2 HS
HN
O
OH
HN
O
NH
2 glutathione
O a) oxidation b) reduction c) neither d) 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 NH
2
H
2
S
OH
I II a) II, IV, I, III b) III, IV, I, II c) IV, III, II, I d) I, III, IV, II
Section: 8.2
Difficulty Level: Easy
1. The major product of the following reaction is,
III
Na
OH
IV
+ 1/2 H
2
Section: 8.2
Difficulty Level: Easy
2. The reagent needed to complete the following reaction is,
H
OH
Section: 8.2
Difficulty Level: Easy
3. The reagent needed to complete the following reaction is,
O
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
H
2
SO
4 heat
Section: 8.2
Difficulty Level: Medium
5. The major product of the following reaction is,
H
2
CrO
4
OH acetone
H
2
O
Section: 8.2
Difficulty Level: Medium
6. The starting material needed to complete the following reaction is,
H
3
PO
4 heat
Section: 8.2
Difficulty Level: Medium
7. The starting material needed to complete the following reaction is,
SOCl
2
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,
OH
O
H
O
S
O
OH
O
H
O
S
O
OH
O H
H
+ H
2
SO
4
+ H
2
O
Section: 8.4
Difficulty Level: Easy
9. The reagent needed to complete the following reaction is,
Section: 8.4
Difficulty Level: Medium
10. The major product of the following reaction is,
H
2
NCH
3
O
O
163

Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.1
Difficulty Level: Easy
1. The following compounds are listed in decreasing order of solubility in water (highest first).
CH
3
CH
2
CH
2
CH
2
O
H > CH
3
CH
2
CH
2
O
H > CH
3
CH
2
O
H > H
3
C
Section: 8.1
Difficulty Level: Medium
2. The following compound is named 1-chloro-2,2-dimethyl-4-pentanol.
O
H
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).
O
O
H
3
C H > CH
3
CH
2
H > CH
3
CH
2
CH
2
O
H > CH
3
CH
2
CH
2
CH
2
Section: 8.2
Difficulty Level: Easy
5. The major product of the reaction of 1-propanol with PCC is propanoic acid.
O
H
164

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).
H
3
C
O
CH
3
> H
3
C
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 <
Section: 8.2, 8.3, and 8.6
Difficulty Level: Easy
10. The strongest acid in the following list is water.
O S
O
H
3
C CH
3
H
3
C CH
3
H H
O
H
3
C
O
H H
3
C
S
H
165

Chapter 8 - Alcohols, Ethers, and Thiols
21. d
22. b
23. b
24. b
25. c
26. d
27. a
12. a
13. c
14. a
15. c
16. c
17. c
18. b
19. d
20. d
5. c
6. b
7. b
8. c
9. c
10. d
11. c
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-dimethyl-
1-propanol: 42g/L
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. SOCl
2
166

Chapter 8 - Alcohols, Ethers, and Thiols
4.
5.
6.
OH
OH
O
7.
8.
OH
OH
O
H
O
S
O
OH
O
H
O
S
O
OH
O H
H
+ H
2
SO
4
+ H
2
O
9. a peracid
167

10.
OH
1. F
2. F
3. T
4. T
5. F
6. T
7. F
8. F
9. F
10. F
NHCH
3
True-False Questions
Chapter 8 - Alcohols, Ethers, and Thiols
168