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

HO

II

OH

OH

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

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(1hydroxypropan2yl)cyclopentanolreactswithamixtureofpotassiumdichromatein

concentratedsulfuricacidatroomtemperature.Whatproductisformed?(help:assumethatyou
havesufficientquantitiesofoxidizertoperformallpossiblereactions.)

HO
K2Cr2O7/H2SO3
HO
HO

HO

HO

II

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(1hydroxypropan2yl)cyclopentanolreactswithpyridiniumchlorochromateindioxane

underreflux.Whatproductisformed?(help:assumethatyouhavesufficientquantitiesof
oxidizertoperformallpossiblereactions.)

HO
K2Cr2O7/H2SO3
HO
HO

HO

HO

III

O
a)
b)
c)
d)

II

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

II
O

ClOS

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

dioxane

HO

OH

HO

II
O

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

OH

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
CH3
a) CH3CHCH
O

Pt / H2

H3PO4
heat
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

Br

diethyl ether

OH

HO

Br

HO

II

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 125 oC.
What is the main product formed?

HBr

OH

Br

dioxane

OH

HO

Br

Br

II

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

HN
O

OH

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
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?

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?

H
O O

(MCPBA)

Cl
THF

O
O

II

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

OH

O
H

a)
b)
c)
d)

OH

O CH3

O CH3

II

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

O O
a)

a)
b)
c)
d)

H+ / H2O

COH

CrO3
H2SO4

O O
b)

CH

a
b
c
d

156

O
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

C
H

a) HOCH2CH2NH2

H2NCH2CH2NH2
b) O

c) HOCH2CH2NHCH2CH2OH
a)
b)
c)
d)

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

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

CH3O H

II.

CH3S

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

H 2S

H 2O

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).

SH

SH
II

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

NH

OH
HN

HO

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

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

OH

+1/2H2

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,

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,

OH
O

H
O

O
O

OH

OH

+ H2SO4
+ H2O
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,

H2NCH3

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

H > CH3CH2CH2

H > CH3CH2

H > H3C

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).

H 3C

H > CH CH
3
2

H > CH3CH2CH2

H > CH3CH2CH2CH2

Section: 8.2
Difficulty Level: Easy
5. The major product of the reaction of 1-propanol with PCC is propanoic acid.

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).

H3C

CH3 > H3C

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.

H 3C

CH3

H 3C

CH3

165

H 3C

H H 3C

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.

Na

2. PCC
3. SOCl2

166

Chapter 8 - Alcohols, Ethers, and Thiols

4.

5.

OH
O
6.

OH

7.

OH
8.

H
OH

O
O

OH

OH

+ 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