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Full Download Test Bank For Introduction To Organic Chemistry 4Th Edition Brown PDF
Full Download Test Bank For Introduction To Organic Chemistry 4Th Edition Brown PDF
Full Download Test Bank For Introduction To Organic Chemistry 4Th Edition Brown PDF
Multiple Choice
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 OH HO
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 III IV
a) III, IV, II, I
b) II, III, IV, I
c) IV, III, II, I
d) 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 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 H2O
I II III IV
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-1-
propanol?
K Cl2 NaCl
c) d)
a) a
b) b
c) c
d) 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
CH3OH
I II III IV
Section: 8.2
Difficulty Level: Medium
9. Which molecules are secondary alcohols?
OH OH
OH
HO
I II 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
K2Cr2O7/H2SO3
HO
HO
O
HO
HO I II
O
O O
O III HO IV
H O
a) I
b) II
c) III
d) 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
O III HO IV
H O
a) I
b) II
c) III
d) 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?
SOCl2
pyridine
HO
O O
Cl
Cl HO
I II
O O
ClOS O
III IV
a) I
b) II
c) III
d) IV
146
Chapter 8 - Alcohols, Ethers, and Thiols
Section: 8.2
Difficulty Level: Medium
13. Which reagents do not effect the following conversion?
HO CH3 Cl CH3
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?
OH
CH3CH2CH2OH CH3CHCH3
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?
PCC
OH
dioxane
O HO H
OH O
HO
I II
O
H
H
O
IV
III
a) I
b) II
c) III
d) 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
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?
CH3
H3PO4 Pt / H2
CH3CHCH2OH
heat
CH3 CH3
a) CH3CHCH b) CH3CHCOH
O O
CH3
c) CH3CHCH3 d) CH3CH2CH2CH3
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 oC. What is the
main product formed?
HBr
OH diethyl ether
HO
OH Br
Br HO
I II
HO HO
III IV
a) I
b) II
c) III
d) 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
OH dioxane
HO
OH Br
Br Br
I II
Br Br
III IV
a) I
b) II
c) III
d) 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 OH H
O N H O
H H H
biotin HO cholesterol
III IV
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?
H3C O
COOH
CH2Cl2
a) b) c) d)
a) a
b) b
c) c
d) d
152
Chapter 8 - Alcohols, Ethers, and Thiols
C OCH
H 3
O O H3C
CH2
cis-1,2-dimethoxycyclohexane R-2-methoxy-1-propanol
I II
OH
H3C
HC OCH3
H3C
OH
2-methoxypropane trans-1,3-cyclohexanediol
III IV
a) I, II
b) III, IV
c) II, III
d) 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) 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 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
(MCPBA)
O O
Cl
THF
O O
O
O I O II
O O
HO
HO
III IV
a) III
b) II
c) I
d) IV
155
Chapter 8 - Alcohols, Ethers, and Thiols
OH
H3PO4 RCO3H CH3 OH
heat
H
OH H
O H OH
O CH3 O CH3
H
H H
I II III IV
a) I
b) II
c) III
d) IV
O
H H+ / H2O CrO3
C C
H2SO4
H H
O O O O O OH O
a) C COH b) C CH c) C CH2OH d) CH COH
a) a
b) b
c) c
d) d
156
Chapter 8 - Alcohols, Ethers, and Thiols
H H
2 C C + H2NCH2CH2NH2
H H
O
a) HOCH2CH2NH2 b) O N
c) HOCH2CH2NHCH2CH2OH d) HOCH2CH2NHCH2CH2NHCH2CH2OH
a) a
b) b
c) c
d) d
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
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 H2S H2O
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?
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
Br
III IV
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 S S O
O NH OH
HN
HO O NH2 O
glutathione disulfide
O
HO
HN
2 HS O
OH
HN
O NH2 O
glutathione
a) oxidation
b) reduction
c) neither
d) both
160
Chapter 8 - Alcohols, Ethers, and Thiols
SH NH2 H2S OH
I II III IV
Na
OH + 1/2 H2
Section: 8.2
Difficulty Level: Easy
2. The reagent needed to complete the following reaction is,
OH O
Section: 8.2
Difficulty Level: Easy
3. The reagent needed to complete the following reaction is,
OH Cl
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 H
O
H H
O S OH
O
O
O S OH
O
+ 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
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).
O O O O
CH3CH2CH2CH2 H > CH3CH2CH2 H > CH3CH2 H > H3C 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).
O O O O
H3C H > CH CH H > CH3CH2CH2 H > CH3CH2CH2CH2 H
3 2
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 3-
methyl-1-butene.
O O O
H3C CH3 > H3C H > H H
< OH < O
O S O O S
H3C CH3 H3C CH3 H H H3C H H3C H
165
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-dimethyl-
1-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
1.
O Na
2. PCC
3. SOCl2
166
Chapter 8 - Alcohols, Ethers, and Thiols
4.
5.
OH
6.
OH
7.
OH
8.
H
OH O H
O
H H
O S OH
O
O
O S OH
O
+ H2SO4
+ H2O
9. a peracid
167
Test Bank for Introduction to Organic Chemistry, 4th Edition: Brown
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
Red-gum, 1109.
Respiration, products of, poisonous, 1359.
Rest, the best time for a child to retire to, 1189.
Revaccination, importance of, 1057.
every seven years, 1057.
Rheumatic fever, flannel vest and drawers, 1328.
Ribs, bulging out of, 1371.
Rice, prepared as an infant’s food, 1039.
Richardson, Dr., ether spray, 1382.
Rickets, 1285.
various degrees of, 1286.
Rocking-chairs, and rockers to cradle, 1079.
Rocking infants to sleep, 1078.
Rooms, ill effects of dark, 1156.
Round shoulders, 1275, 1370.
Round-worm, 1282.
Running scall, 1289.
Rupture, 1026, 1027.
Rusks, 1039.
Tape-worm, 1282.
Taste for things refined, 1156.
Tea, on giving a child, 1147.
green, the ill effects of, 1147, 1336.
Teeth, attention to, importance of, 1364.
child should not have meat until he have cut several, 1132.
the diet of a child who has cut all his, 1132.
and gums, 1364.
right way of brushing, 1365.
appearance and number of first set of, 1063.
appearance and number of second set of, 1194.
second crop of, 1194.
Teething, 1062.
Teething, eruptions from, 1074.
frequent cause of sickness, 1111.
fruitful source of disease, 1070.
purging during, 1073.
restlessness from, 1294.
second, 1194.
symptoms and treatment of painful, 1071.
in town and country, 1073.
Temperature and ventilation of a nursery, 1150.
of a warm bath, 1294.
Thread-worm, 1282.
Throats, sore, precautions to prevent, 1370.
Thrush, cause, symptoms, prevention, and cure of, 1112.