Download test bank for organic chemistry 2nd edition by klein

Test Bank for Organic Chemistry 2nd Edition by Klein
Link download full: />Chapter Fourteen
Topic: Introduction to Ethers
Section: 14.1
1. Which of the following compounds is(are) classified as ethers?
A) I
B) II & IV
C) III
D) I & III
E) all of these Ans: E
Topic: Nomenclature of Ethers
Section: 14.2
Difficulty Level: Easy
2. What is the common name for CH3CH2CH2OCH2CH2CH3?
A) Dibutylether
B) 1-propoxypropane
C) 1-propoxyhexane
D) dipropyl ether
E) none of these Ans: D
Topic: Nomenclature of Ethers
Section: 14.2
Difficulty Level: Easy
3. What is the common name for (CH3)2CHCH2OCH(CH3)2?
A) Diisobutylether
B) isobutyl isopropyl ether
C) sec-butyl isopropyl ether
D) Diisopropylether
E) none of these
Ans: B
Topic: Nomenclature of Ethers
Section: 14.2

Difficulty Level: Easy


4. What is the IUPAC name for CH3CH2CH2CH2OCH2CH3?
A) 1-ethoxybutane
B) 1-butoxyethane
C) ethyl butyl ether
D) 1-ethoxyhexane
E) none of these Ans: A
Topic: Nomenclature of Ethers
Section: 14.2
Difficulty Level: Medium
5. What is the common name for the following compound?
A) 1-butoxybutane
B) sec-butyl isopropyl ether
C) sec-butyl t-butyl ether
D) n-butyl isopropyl ether
E) none of these Ans: C
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
6. What is the IUPAC name for CH3CH2OCH2CH2CH2CH2OCH2CH3?
A) 1,4-ethoxyoctane
B) diethoxy butyl ether
C) 1,2-diethoxymethane
D) 1,2-diethoxyhexane
E) 1,4-diethoxybutane Ans: E
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium

7. What is the correct structure for benzyl phenyl ether?
A) I
B) II
C) III
D) IV
E) none of these


Ans: D
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
8. What is the correct structure for dibenzyl ether?
A) I
B) II
C) III
D) IV
E) none of these
Ans: B
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
9. What is the IUPAC name for the following compound?
Ans: 3-isopropoxy-2-methyloctane
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
10. What is the IUPAC name for the following compound?
Ans: 1-ethoxy-1-methoxy-3-propylcyclohexane
Topic: Nomenclature

Section: 14.2
Difficulty Level: Medium
11. What is the IUPAC name for the following compound?
Ans: E-4-isopropoxy-4,5-dimethylhex-2-ene
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
12. What is the IUPAC name for the following compound?


Ans: (1S,3S)-1-ethoxy-3-methylcyclohexane
Topic: Nomenclature
Section: 14.2
Difficulty Level: Hard
13. What is the IUPAC name for the following compound?
Ans: 1,1,1-triethoxyethane
Topic: Nomenclature
Section: 14.2
Difficulty Level: Hard
14. Provide the structure for 2-iodo-4-isopropyl-1-methoxybenzene. Ans:
Topic: Nomenclature
Section: 14.2
Difficulty Level: Hard
15. Provide an IUPAC name for the following compound.
Ans: 4-t-butyl-1-ethoxy-2-methylbenzene
Topic: Nomenclature
Section: 14.2
Difficulty Level: Hard
16. Provide the structure for (2S,5R)-5-ethoxy-2-octanol. Ans:
Topic: Nomenclature

Section: 14.2
Difficulty Level: Hard
17. Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane. Ans:
Topic: Nomenclature
Section: 14.2
Difficulty Level: Easy
18. Draw all constitutional isomers with molecular formula C4H8O having an ether
functional group and provide the IUPAC name for each isomer. Ans:
Topic: Nomenclature
Section: 14.2


Difficulty Level: Medium
19. Draw all constitutional isomers with molecular formula C6H14O having an ether
functional group and provide the IUPAC name for each isomer Ans:
Topic: Physical Properties
Section: 14.3
Difficulty Level: Easy
20. Which one of the following compounds will have the highest boiling point?
A) CH3CH2CH2CH2CH3
B) CH3CH2CH2CH2OH
C) CH3CH2CH2OCH3 D) CH3CH2CH2Cl
E) CH3CH2OCH2CH3
Ans: B
Topic: Physical Properties
Section: 14.3
Difficulty Level: Easy
21. Which one of the following compounds will have the highest boiling point?
A) CH3CH2CH2CH2CH3
B) CH3CH2CH2CH2OH

C) CH3CH2CH2OCH3
D) CH3CH2CH2Cl
E) CH3CH2OCH2CHOH
Ans: E
Topic: Physical Properties
Section: 14.3
Difficulty Level: Easy
22. Which one of the following compounds will be least soluble in water?
A) diethyl ether
B) methyl propyl ether
C) 1-butanol
D) 2-butanol
E) pentane Ans: E
Topic: Physical Properties
Section: 14.3
Difficulty Level: Medium


23. Rank the following compounds in decreasing order of boiling points (highest to
lowest)
A) II>IV>I>III
B) I>IV>II>III
C) IV>I>II>III
D) III>II>I>IV
E) IV>II>I>III Ans: C
Topic: Physical Properties
Section: 14.3
Difficulty Level: Medium
24. Rank the following compounds in decreasing order of water solubility (highest
to lowest)

A) II>IV>I>III
B) I>IV>II>III
C) IV>I>II>III
D) III>II>I>IV
E) IV>III>I>II Ans: E
Topic: Physical Properties
Section: 14.3
Difficulty Level: Medium
25. Which one of the following compounds has highest boiling point?
Ans: III
Topic: Crown ethers
Section: 14.4
Difficulty Level: Medium
26. What is the IUPAC name for the following compound?
A) 15-crown-5
B) 15-crown-4
C) 5-crown-15
D) 15-crown-15
E) none of these Ans: A
Topic: Crown ethers


Section: 14.4
Difficulty Level: Medium
27. What is the correct IUPAC name for the following compound?
A) 12-crown-5
B) 12-crown-4
C) 4-crown-12
D) 12-crown-12
E) none of these Ans: B

Topic: Crown ethers
Section: 14.4
Difficulty Level: Easy
28. Which of the following crown ether solvates lithium ions?
A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these Ans: B
Topic: Crown ethers
Section: 14.4
Difficulty Level: Easy
29. Which of the following crown ether solvates potassium ions?
A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these Ans: D
Topic: Crown ethers
Section: 14.4
Difficulty Level: Easy
30. Which of the following crown ether solvates sodium ions?
A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6


E) none of these Ans: C
Topic: Crown ethers

Section: 14.4
Difficulty Level: Medium
31. Identify the missing reagent needed to carry out the following transformation.
A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these Ans: C
Topic: Crown ethers
Section: 14.4
Difficulty Level: Medium
32. Identify the missing reagent needed to carry out the following transformation.
A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these
Ans: B
Topic: Crown ethers
Section: 14.4
Difficulty Level: Hard
33. Identify the missing reagent needed to carry out the following transformation.
Ans: 18-crown-6
Topic: Crown ethers
Section: 14.4
Difficulty Level: Hard
34. Identify the missing reagent needed to carry out the following transformation.
Ans: 18-crown-6
Topic: Preparation of ethers

Section: 14.5
Difficulty Level: Easy
35. Predict the product for the following reaction.
A) Propene
B) Diethyl ether
C) 1-hexanol
D) 1-propoxypropane Ans: D
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Medium
36. Predict the product for the following reaction.
Ans:
Topic: Preparation of Ethers
Section: 14.5
Difficulty Level: Hard
37. Provide a curved arrow mechanism for the formation of the product.
Ans:
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Medium
38.Can you prepare diisopropyl ether as major product by heating 2-propanol in
the presence of sulfuric acid? Explain your answer.
Ans: No. Secondary and tertiary alcohols undergo elimination reactions when
heated in the presence of a strong acid, such as sulfuric acid. The major product is
an alkene and not an ether. 2-propanol is a secondary alcohol and it will yield
propene as the major product.
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Medium

39. Which one of the following reactions would produce t-butyl methyl ether in high
yield?


A) t-butyl chloride + sodium methoxide
B) t-butanol + methanol in presence of H2SO4 at 140 C
C) t-butyl bromide + bromomethane in presence of NaOH
D) sodium t-butoxide + bromomethane Ans: D
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Medium
40. Which one of the following reactions would produce t-butyl methyl ether in
high yield?
A) CH3ONa + (CH3)3CBr
B) CH3OH + (CH3)3COH in presence of H2SO4 at 140
C
C) CH3Cl + (CH3)3CBr in presence of NaOH
D) (CH3)3CONa + CH3Br Ans: D
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Medium
41. Which one of the following reactions would produce (S)-3-methoxyheptane in
high yield?
A) sodium (S)-3-heptoxide + bromomethane
B) sodium (R)-3-heptoxide + bromomethane
C) sodium methoxide + (S)-3-bromoheptane
D) sodium methoxide + (R)-3-bromoheptane Ans: A
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Medium

42. Predict the product for the following reaction.
Ans:
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Medium
43. Provide the reagents necessary to carry out the following conversion.


Ans: 1. PBr3
2.
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Hard
44.Predict the product for the following reaction.
Ans:
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Medium
45. Provide the reagents necessary to prepare the following compound using a
Williamson ether synthesis. Ans:
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Medium
46.Provide the reagents necessary to prepare the following compound using
Williamson ether synthesis. Ans:
Topic: Preparation of ethers
Section: 14.5
Difficulty Level: Hard
47. Predict the product for the following reaction and provide a curved arrow
mechanism for the formation of the product.

Ans:
Mechanism
Topic: Preparation of Ethers
Section: 14.5
Difficulty Level: Medium
48. Predict the product for the following reaction.
A) 3-methyl-3-pentanol
B) 3-ethoxy-3-methylpentane
C) 3-methyl-2-pentanol


D) 2-ethoxy-3-methylpentane
E) 1-ethoxy-3-methylpentane Ans: B
Topic: Preparation of Ethers
Section: 14.5
Difficulty Level: Hard
49.Predict the product for the following reaction.
A) 1-ethyl-1-cyclohexanol
B) 2-ethoxy-1-ethylcyclohexane
C) 1-ethoxy-1-ethylcyclohexane
D) 2-ethoxy-3-ethylcyclohexane
E) 1-ethoxy-2-ethylcyclohexane Ans: C
Topic: Preparation of Ethers
Section: 14.5
Difficulty Level: Hard
50.Predict the product for the following reaction.
A) 2-methyl-1-hexanol
B) 2-methoxy-2-methylhexane
C) 1-methoxy-2-methylhexane
D) 2-methoxy-3-methylhexane

E) 2-methyl-2-hexanol Ans: B
Topic: Preparation of Ethers
Section: 14.5
Difficulty Level: Hard
51. Predict the product for the following reaction.
Ans:
Topic: Preparation of Ethers
Section: 14.5
Difficulty Level: Hard
52. . Predict the product for the following reaction. Ans:
Topic: Preparation of Ethers
Section: 14.5
Difficulty Level: Hard


53. . Provide the reagents necessary to prepare the following compound using
alkoxymercuration-demercuration.
Ans:
OR
OR
Topic: Preparation of Ethers
Section: 14.5
Difficulty Level: Hard
54. . Provide the reagents necessary to carry out the following conversion. Ans:
Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Easy
55. Predict the product(s) for the following reaction.
A) ethanol + 1-bromopropane B)
1-propanol + bromoethane

C) 1-propanol + ethanol
D) 1-bromopropane + bromoethane
E) none of these Ans: D
Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Easy
56. Predict the product(s) for the following reaction.
A) ethanol + phenol
B) phenol + iodoethane
C) iodobenzene + ethanol
D) iodobenzene + iodoethane
E) none of these Ans: B
Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Medium
57. Predict the product(s) for the following reaction.


A) I
B) II
C) III
D) IV
E) V
Ans: C
Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Medium
58. Predict the product(s) for the following reaction.
A) I
B) II

C) III
D) IV
E) V
Ans: B
Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Medium
59. Predict the product(s) for the following reaction and provide a curved arrow
mechanism for the formation of the product.
Ans:
Mechanism
Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Hard
60. Predict the product(s) for the following
reaction. Ans:
Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Hard


61. Predict the product(s) for the following reaction and provide a curved arrow
mechanism for the formation of the product.
Ans:
Mechanism
Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Hard
62. Predict the product(s) for the following reaction.
Ans:

Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Medium
63. Predict the product(s) for the following reaction.
Ans:
Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Medium
64. Explain why long-term storage of ethers can be dangerous.
Ans: Ethers undergo autooxidation in the presence of atmospheric oxygen via a
radical mechanism to form hydroperoxides. These hydroperoxides are unstable and
can explode on heating.
Topic: Nomenclature of epoxides
Section: 14.7
Difficulty Level: Easy
65. What is the IUPAC name for the following compound?
A) 3-ethyl-2-methyloxirane
B) 2-ethyl-3-methyloxirane
C) 2-ethyl-1-methyloxypentane
D) 1-ethyl-2-methyloxypentane
E) none of these Ans: B
Topic: Nomenclature of epoxides


Section: 14.7
Difficulty Level: Medium
66.What is the IUPAC name for the following compound?
A) 2-ethyl-3-isopropyl-2-methyloxirane
B) 1-ethyl-2-isopropyl-1-methyloxirane
C) 2,4-dimethyloxyhexane

D) 1-ethyl-2,4-dimethyloxyhexane
E) 3-ethyl-2-isopropyl-3-methyloxirane Ans: A
Topic: Nomenclature of epoxides
Section: 14.7
Difficulty Level: Medium
67. Provide the structure for tetrahydrofuran. Ans:
Topic: Nomenclature of epoxides
Section: 14.7
Difficulty Level: Medium
68. Provide the structure for oxetane.
Ans: Topic: Nomenclature of epoxides
Section: 14.7
Difficulty Level: Medium
69.Provide the IUPAC name for the following compound.
Ans: (2S, 3S)-2-ethyl-3-isopropyloxirane
Topic: Nomenclature of epoxides
Section: 14.7
Difficulty Level: Medium
70. Provide the IUPAC name for the following compound.
Ans: (2S, 3R)-2-ethyl-3-phenyloxirane
Topic: Nomenclature of epoxides
Section: 14.7
Difficulty Level: Medium
71. Provide the common name for the following compound.


Ans: 1,4-dioxane
Topic: Nomenclature of epoxides
Section: 14.7
Difficulty Level: Medium

72. Provide the IUPAC name for the following compound.
Ans: (1S,2R)-1-methyl-1,2-epoxycyclohexane
Topic: Nomenclature of epoxides
Section: 14.7
Difficulty Level: Medium
73. Provide the structure for (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane. Ans:
Topic: Nomenclature of epoxides
Section: 14.7
Difficulty Level: Medium
74. Provide the structure for (R)-2,2,3-trimethyl-3-phenyloxirane. Ans:
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
75. Predict the product for the following reaction. (E)-2-pentene + mCPBA
A) I
B) II
C) III
D) IV
Ans: D
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
76. Predict the product for the following reaction. (Z)-3-hexene
+ mCPBA
A) I
B) II
C) III


D) IV

Ans: A
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
77. Predict the product for the following reaction.
A) I
B) II
C) III
D) IV
Ans: C
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
78. Predict the product for the following reaction.
1-methylcyclohexene + mCPBA Ans:
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
79. Provide the reagents necessary to carry out the following conversion.
Ans: mCPBA
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
80. Predict the product for the following reaction.
A) I
B) II
C) III
D) IV
Ans: D
Topic: Preparation of epoxides

Section: 14.8


Difficulty Level: Medium
81. Predict the product for the following reaction.
Ans:
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
82. Provide the structure(s) of the product(s) in the following reaction
sequence. Ans:
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
83.Predict the product for the following reaction.
Ans:
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
84. Provide the reactants necessary to prepare the following
compound. Ans:
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
85. Provide the reactants necessary to prepare the following compound.
Ans:
Topic: Preparation of epoxides
Section: 14.8
Difficulty Level: Medium
86. Provide the reactants necessary to prepare the following

compound. Ans:


Topic: Preparation of epoxides
Section: 14.9
Difficulty Level: Medium
87. Predict the product for the following reaction.
Ans:
Topic: Preparation of epoxides
Section: 14.9
Difficulty Level: Medium
88. Predict the product for the following
reaction. Ans:
Topic: Preparation of epoxides
Section: 14.9
Difficulty Level: Medium
89. Predict the product for the following
reaction. Ans:
Topic: Preparation of epoxides
Section: 14.9
Difficulty Level: Medium
90. Predict the product for the following
reaction. Ans:
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Easy
91. Predict the product(s) for the following reaction.
A) I
B) II
C) III

D) IV
E) none of these Ans: C
Topic: Reactions of epoxides


Section: 14.10
Difficulty Level: Easy
92. Predict the product(s) for the following reaction.
A) I
B) II
C) III
D) IV
E) none of these Ans: A
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Easy
93. Predict the product(s) for the following reaction.
A) I
B) II
C) III
D) IV
E) none of these Ans: B
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Medium
94. Predict the product(s) for the following reaction.
A) I
B) II
C) III
D) IV

E) none of these Ans: A
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Medium
95. Predict the product(s) for the following reaction.
A) I
B) II
C) III


D) IV
E) none of these
Ans: C
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Medium
96.Provide the reagents necessary to carry out the following conversion.
Ans: HCl
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Medium
97. Provide the reagents necessary to carry out the following conversion.
Ans: CH3OH/H2SO4
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Medium
98. Predict the product(s) for the following reaction.
A) I
B) II
C) III

D) IV
E) none of these Ans: A
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Easy
99.Predict the product(s) for the following reaction.
A) I
B) II
C) III
D) IV
E) none of these Ans: C


Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Easy
100.Predict the product(s) for the following reaction.
A) I
B) II
C) III
D) IV
E) none of these Ans: D
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Medium
101. Predict the product(s) for the following reaction.
Ans:
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Medium

102. Predict the product(s) for the following reaction.
Ans:
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Medium
103. Provide the reagents necessary to carry out the following conversion.
Ans: 1. mCPBA
2. CH3MgBr
3. H2O
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Hard
104. Provide the reagents necessary to carry out the following conversion.
Ans: 1. LiAlH4


2. H2O
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Hard
105. Provide the reagents necessary to carry out the following conversion.
Ans: 1. mCPBA
2. NH3
Topic: Reactions of epoxides
Section: 14.10
Difficulty Level: Hard
106. Provide the reagents necessary to carry out the following conversion.
Ans: 1. 2.
H2O
Topic: Reactions of epoxides

Section: 14.10
Difficulty Level: Hard
107. Provide a stepwise curved arrow mechanism for the following reaction.
Ans:
Topic: Nomenclature of Thiols /sulfides
Section: 14.11
Difficulty Level: Easy
108. What is the correct structure for 3-methyl-1-hexanethiol?
Ans:
Topic: Nomenclature of Thiols /sulfides
Section: 14.11
Difficulty Level: Medium
109. What is the correct structure for phenylthiol?
Ans:
Topic: Nomenclature of Thiols /sulfides


Section: 14.11
Difficulty Level: Medium
110. What is the IUPAC name for the following compound?
Ans: 5-methyl-2-heptanethiol
Topic: Nomenclature of Thiols /sulfides
Section: 14.11
Difficulty Level: Hard
111. What is the IUPAC name for the following compound?
Ans: 5-mercapto-2-methyl-1-hexanol
Topic: Nomenclature of Thiols /sulfides
Section: 14.11
Difficulty Level: Medium
112. What is the common name for the following compound?

Ans: Methyl pentyl sulfide
Topic: Nomenclature of Thiols /sulfides
Section: 14.11
Difficulty Level: Medium
113. What is the IUPAC name for the following compound?
Ans: 2-ethylthiohexane
Topic: Preparation of Thiols /sulfides
Section: 14.11
Difficulty Level: Easy
114. Predict the product for the following reaction.
Ans:
Topic: Preparation of Thiols /sulfides
Section: 14.11
Difficulty Level: Medium
115. Predict the product for the following reaction.