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Chapter Fourteen Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 1. What is the common name for CH3CH2CH2OCH2CH2CH3? A) B) C) D) E)
dibutylether 1-propoxypropane 1-propoxyhexane dipropyl ether none of these Ans: D
Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 2. What is the common name for (CH3)2CHCH2OCH(CH3)2? A) B) C) D) E)
diisobutylether isobutyl isopropyl ether sec-butyl isopropyl ether diisopropylether none of these Ans: B
Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 3. What is the IUPAC name for CH3CH2CH2CH2OCH2CH3? A) B) C) D) E)
1-ethoxybutane 1-butoxyethane ethyl butyl ether 1-ethoxyhexane none of these Ans: A
Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Medium
4. What is the common name for the following compound? O
A) B) C) D) E)
1-butoxybutane sec-butyl isopropyl ether sec-butyl t-butyl ether n-butyl isopropyl ether none of these Ans: C
Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 5. A) B) C) D) E)
What is the IUPAC name for CH3CH2OCH2CH2CH2CH2OCH2CH3? 1,4-ethoxyoctane diethoxy butyl ether 1,2-diethoxymethane 1,2-diethoxyhexane 1,4-diethoxybutane Ans: E
Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 6. What is the correct structure for benzyl phenyl ether?
H3C
O
CH2OCH2
I
II
O
III
A) B) C) D) E)
I II III IV none of these Ans: D
CH3
CH2O
IV
Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 7. What is the correct structure for dibenzyl ether? O
CH2OCH2
I
II CH3
H3C
O
III
A) B) C) D) E)
CH3
CHOCH CH3 CH3
I II III IV none of these Ans: B
Topic: Nomenclature Section: 14.4 Difficulty Level: Hard 8. What is the IUPAC name for the following compound? O O
O
O
A) B) C) D) E)
15-crown-5 15-crown-4 5-crown-15 15-crown-15 none of these Ans: A
Topic: Nomenclature Section: 14.4 Difficulty Level: Hard
O
CH3CH2OCOCH2CH3 IV
OCH2CH3
9. What is the correct IUPAC name for the following compound?
A) B) C) D) E)
O
O
O
O
12-crown-5 12-crown-4 4-crown-12 12-crown-12 none of these Ans: B
Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 10. What is the IUPAC name for the following compound? O
Ans: 3-isopropoxy-2-methyloctane Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 11. What is the IUPAC name for the following compound? O
O
Ans: 1-ethoxy-1-methoxy-3-propylcyclohexane Topic: Nomenclature Section: 14.2 Difficulty Level: Medium
12. What is the IUPAC name for the following compound? O
Ans: E-4-isopropoxy-4,5-dimethylhex-2-ene Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 13. What is the IUPAC name for the following compound? CH3
CH3CH2OCOCH2CH3 OCH2CH3
Ans: 1,1,1-triethoxyethane Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 14. Provide the structure for (2S,5R)-5-ethoxy-2-octanol. OCH2CH3
Ans:
OH
Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 15. Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane. Ans:
O
OCH3 OCH3
Topic: Physical Properties Section: 14.3 Difficulty Level: Easy
16. A) B) C) D) E)
Which one of the following compounds will have the highest boiling point? CH3CH2CH2CH2CH3 CH3CH2CH2CH2OH CH3CH2CH2OCH3 CH3CH2CH2Cl CH3CH2OCH2CH3 Ans: B
Topic: Physical Properties Section: 14.3 Difficulty Level: Easy 17. A) B) C) D) E)
Which one of the following compounds will have the highest boiling point? CH3CH2CH2CH2CH3 CH3CH2CH2CH2OH CH3CH2CH2OCH3 CH3CH2CH2Cl CH3CH2OCH2CHOH Ans: E
Topic: Physical Properties Section: 14.3 Difficulty Level: Easy 18. A) B) C) D) E)
Which one of the following compounds will be least soluble in water? diethyl ether methyl propyl ether 1-butanol 2-butanol pentane Ans: E
Topic: Physical Properties Section: 14.3 Difficulty Level: Medium
19. Rank the following compounds in decreasing order of boiling points (highest to lowest)
A) B) C) D) E)
CH3CH2CH2CH2OH I II>IV>I>III I>IV>II>III IV>I>II>III III>II>I>IV IV>II>I>III Ans: C
CH3CH2OCH2CH3 II
CH3OCH3 III
HOCH2CH2CH2OH IV
Topic: Physical Properties Section: 14.3 Difficulty Level: Medium 20. Rank the following compounds in decreasing order of water solubility (highest to lowest) CH3CH2CH2CH2OH
A) B) C) D) E)
I
CH3CH2OCH2CH2CH3 II
CH3CH2OCH2CH2OH III
CH3CH2OH IV
II>IV>I>III I>IV>II>III IV>I>II>III III>II>I>IV IV>III>I>II Ans: E
Topic: Physical Properties Section: 14.3 Difficulty Level: Medium 21. Which one of the following compounds will have highest boiling point? O
O
HO
Ans: III
I
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Easy
II
O
OH
HO
III
HO
IV
22. Predict the product for the following reaction. H2SO4 2 CH3CH2CH2OH 1400C A) propene B) Diethyl ether C) 1-hexanol D) 1-propoxypropane Ans: D Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 23. Predict the product for the following reaction. H2SO4 2-cyclopentylethanol 1400C O Ans:
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 24. Provide a curved arrow mechanism for the formation of the product. O
H2SO4
O HO
OH O
Ans: O HO
O
OH
HO
O H
O
S
OH2
+
OH
O
O
+ H2SO4 O O O
S
H O
OH
O
S O
O
O
O OH
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 25. 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 26. Which one of the following reactions would produce t-butyl methyl ether in high yield? A) B) C) D)
t-butyl chloride + sodium methoxide t-butanol + methanol in presence of H2SO4 at 140°C t-butyl bromide + bromomethane in presence of NaOH Sodium t-butoxide + bromomethane Ans: D
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 27. Which one of the following reactions would produce t-butyl methyl ether in high yield? A) B) C) D)
CH3ONa + (CH3)3CBr CH3OH + (CH3)3COH in presence of H2SO4 at 140°C CH3Cl + (CH3)3CBr in presence of NaOH (CH3)3CONa + CH3Br Ans: D
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium
28. 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 29. Predict the product for the following reaction. OH
1. NaH 2. CH3CH2CH2I
Ans:
OCH2CH2CH3
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 30. Provide the reagents necessary to carry out the following conversion. OH
Ans:
1. PBr3 2. ONa
O
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Hard 31. Predict the product for the following reaction. OH Br
NaOH heat
Ans: O
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 32. Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis. O
Ans:
ONa
+ CH3CH2CH2Cl
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 33. Provide the reagents necessary to prepare the following compound using Williamson synthesis. (CH3)2CHCH2OCH(CH3)2 Ans: (CH3)2CHCH2Cl + (CH3)2CHONa Topic: Preparation of ethers Section: 14.5 Difficulty Level: Hard
34. Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product. NaOH Br
OH
Ans:
O
Mechanism H Br
O
OH
+ NaBr O
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Medium 35. Predict the product for the following reaction. 3-methyl-2-pentene
A) B) C) D) E)
1. Hg(OAc)2, CH3CH2OH 2. NaBH4
3-methyl-3-pentanol 3-ethoxy-3-methylpentane 3-methyl-2-pentanol 2-ethoxy-3-methylpentane 1-ethoxy-3-methylpentane Ans: B
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard
Br
O
Na
36. Predict the product for the following reaction. 1-ethyl-1-cyclohexene
A) B) C) D) E)
1. Hg(OAc)2, CH3CH2OH 2. NaBH4
1-ethyl-1-cyclohexanol 2-ethoxy-1-ethylcyclohexane 1-ethoxy-1-ethylcyclohexane 2-ethoxy-3-ethylcyclohexane 1-ethoxy-2-ethylcyclohexane Ans: C
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 37. Predict the product for the following reaction. 1. Hg(OAc)2, CH3OH 2. NaBH4
A) B) C) D) E)
2-methyl-1-hexanol 2-methoxy-2-methylhexane 1-methoxy-2-methylhexane 2-methoxy-3-methylhexane 2-methyl-2-hexanol Ans: B
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 38. Predict the product for the following reaction.
1. Hg(OAc)2, 2. NaBH4
Ans: O
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard
OH
39. Predict the product for the following reaction. . 1. Hg(OAc)2, CH3CH2OH 2. NaBH4
Ans: O
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 40. Provide the reagents necessary to prepare the following compound using . alkoxymercuration-demercuration. O
OH
Ans: 1. Hg(OAc)2, 2. NaBH4
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 41. Provide the reagents necessary to carry out the following conversion. . OC(CH3)3
Ans:
1. Hg(OAc)2, (CH3)3COH 2. NaBH4
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Easy
42. Predict the product(s) for the following reaction. HBr
O
A) B) C) D) E)
excess
ethanol + 1-bromopropane 1-propanol + 1-bromoethane 1-propanol + ethanol 1-bromopropane + 1-bromoethane none of these Ans: D
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Easy 43. Predict the product(s) for the following reaction. O
HI excess
A) B) C) D) E)
ethanol + phenol phenol + 1-iodoethane iodobenzene + ethanol iodobenzene + 1-iodoethane none of these Ans: B
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium
44. Predict the product(s) for the following reaction. HBr O
excess
CH2OH
Br
+
III
II
I OH
OCH2Br
I II III IV V Ans: C
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium
CH2Br
OH
+
+
A) B) C) D) E)
CH2OH
OH
CH2Br
Br
+
+
IV
V
45. Predict the product(s) for the following reaction. HI excess
O
I
O
I
I
I
OH
III
II
OH
+
I
O
A) B) C) D) E)
I
V
IV
I II III IV V Ans: B
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 46. Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product. HBr excess
O
Br
Ans: Br
Mechanism
O
O H
Br
H
Br
H
Br Br
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard
Br
OH
+ H2O
Br
OH2
Br
Br
47. Predict the product(s) for the following reaction. O
HI excess O
Ans:
I
2 I
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard 48. Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product. HBr excess
O
Ans: Br
OH
Mechanism Br O
O H
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard
Br
Br H
OH
49. Predict the product(s) for the following reaction. HI O
1 mol
Ans:
OH I
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 50. Predict the product(s) for the following reaction. O
HBr excess
Ans: Br
+ Br
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 51. 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
52. What is the IUPAC name for the following compound? O
A) B) C) D) E)
2-ethyl-1-methyloxirane 1-ethyl-2-methyloxirane 2-ethyl-1-methyloxypentane 1-ethyl-2-methyloxypentane none of these Ans: B
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 53. What is the IUPAC name for the following compound? O
A) B) C) D) E)
2-ethyl-1-isopropyl-2-methyloxirane 1-ethyl-2-isopropyl-1-methyloxirane 2,4-dimethyloxyhexane 1-ethyl-2,4-dimethyloxyhexane none of these Ans: B
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 54. Provide the structure for tetrahydrofuran. Ans: O
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium
55. Provide the structure for oxetane. Ans:
O
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 56. Provide the IUPAC name for the following compound. O
Ans: (1S, 2S)-1-ethyl-2-isopropyloxirane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 57. Provide the IUPAC name for the following compound. O
Ans: (1S, 2R)-1-ethyl-2-phenyloxirane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 58. Provide the common name for the following compound. O
O
Ans: 1,4-dioxane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium
59. Provide the IUPAC name for the following compound.
O
Ans: (1S,2R)-1-methyl-1,2-epoxycyclohexane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 60. Provide the structure for (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane. Ans:
O
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 61. Provide the structure for 1,1,2-trimethyl-2-phenyloxirane. Ans: O
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium
62. Predict the product for the following reaction. (E)-2-pentene + mBA O
I
A) B) C) D)
O
II O
O
III
IV
I II III IV Ans: D
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 63. Predict the product for the following reaction. (Z)-3-hexene + mBA O
I
A) B) C) D)
O
II O
O
III
IV
I II III IV Ans: A
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium
64. Predict the product for the following reaction. O
+ CH3COOH
OH
OH
A) B) C) D)
I II III IV Ans: C
O O
III
II
I
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 65. Predict the product for the following reaction. 1-methylcyclohexene + mBA Ans: O
+ enantiomer
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 66. Provide the reagents necessary to carry out the following conversion. O
Ans: mBA
O
+ enantiomer IV
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 67. Predict the product for the following reaction. 1. Br2/H2O 2. NaOH Br
Br
OH Br
OH
A) B) C) D)
I II III IV Ans: D
II
I
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 68. Predict the product for the following reaction. 1. Br2/H2O 2. NaOH
Ans:
O
+ enantiomer
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium
O
III
IV
69. Provide the structure(s) of the product(s) in the following reaction sequence. Br2/H2O
A
NaOH
B
Ans: OH
+ enantiomer
O
Br
B
A
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 70. Predict the product for the following reaction. O H
CH3 OOH
+ H
Cl
Ans: O H
CH3
+ enantiomer H
Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium
+ enantiomer
71. Predict the product for the following reaction. (CH3)3COOH OH
Ti[OCH(CH3)2]4 (+) DET OH
Ans:
O
Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium 72. Predict the product for the following reaction. OH
(CH3)3COOH Ti[OCH(CH3)2]4 (+) DET
Ans:
OH
O
Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium
73. Predict the product for the following reaction. OH
(CH3)3COOH Ti[OCH(CH3)2]4 (-) DET
OH
Ans:
O
Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium 74. Predict the product for the following reaction. HO
(CH3)3COOH Ti[OCH(CH3)2]4 (-) DET
Ans: HO
O
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy
75. Predict the product(s) for the following reaction. O
H3O+
OH
OH
H O
OH
A) B) C) D) E)
OH
OH
+ enantiomer
II
I
IV
III
I II III IV none of these Ans: C
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy 76. Predict the product(s) for the following reaction. O
HBr
H OH
Br
Br
O
Br
A) B) C) D) E)
I
HO
I II III IV none of these Ans: A
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy
II
III
Br
IV
77. Predict the product(s) for the following reaction. O
CH3OH/H2SO4
OCH3
H
HO
OH
I
A) B) C) D) E)
H
H3CO
OH
OCH3
HO
H3CO
II
IV
III
I II III IV none of these Ans: B
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 78. Predict the product(s) for the following reaction. O
CH3OH/H2SO4
OCH3
OH
OCH3
I
A) B) C) D) E)
I II III IV none of these Ans: A
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium
OCH3
OCH3
OH
II
OH
III
OH
Iv
79. Predict the product(s) for the following reaction.
O
CH3CH2OH/H2SO4
I
A) B) C) D) E)
OCH2CH3 CH3
OH
CH3 OH
CH3
OCH2CH3
OCH2CH3
OCH2CH3 CH3
OH
III
II
OH
IV
I II III IV none of these Ans: C
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 80. Provide the reagents necessary to carry out the following conversion. OH
O
Cl
Ans: HCl Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 81. Provide the reagents necessary to carry out the following conversion. H3C
O
CH3 H3CO
OH H
Ans: CH3OH/H2SO4
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 82. Predict the product(s) for the following reaction. O
1. NaSH 2. H2O
HO
H
HS
H
SH
I
A) B) C) D) E)
I II III IV none of these Ans: A
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy
NaO
HO
OH
II
OH
OH
III
IV
83. Predict the product(s) for the following reaction. O
1. NaCN 2. H2O OH
OH
I
II
+ enantiomer
CN
OH
OH
+ enantiomer
A) B) C) D) E)
CN
CN
CN
+ enantiomer III
IV
I II III IV none of these Ans: C
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy 84. Predict the product(s) for the following reaction.
O
1. CH3ONa 2. H2O
I
A) B) C) D) E)
OCH3
OH
CH3 OH
CH3
CH3
OCH3
OCH3
OH
I II III IV none of these Ans: D
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium
II
III
CH3 OH
OCH3
IV
85. Predict the product(s) for the following reaction. O
1. CH3MgBr 2. H2O OH
Ans:
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 86. Predict the product(s) for the following reaction. H3C
O
1. (CH3)2NH 2. H2O
Ans:
H3C
OH N(CH3)2
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium
87. Provide the reagents necessary to carry out the following conversion. CH3 OH
+ enantiomer CH3
Ans:
1. mBA 2. CH3MgBr 3. H2O
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 88. Provide the reagents necessary to carry out the following conversion.
O
Ans:
OH
1. LiAlH4 2. H2O
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 89. Provide the reagents necessary to carry out the following conversion. OH
NH2
Ans:
1. mBA 2. NH3
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard
+ enatiomer
90. Provide the reagents necessary to carry out the following conversion. OH
O
Ans:
MgBr
1. 2. H2O Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 91. Provide a stepwise curved arrow mechanism for the following reaction. OH
O
H3O+ heat
OH H
Ans: O
O H
O
H
+ H2O
H OH
OH
H2O
H2O O H
OH
+ H3O+
OH
H
Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Easy 92. What is the correct structure for 3-methyl-1-hexanethiol? Ans: HS
Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 93. What is the correct structure for phenylthiol? Ans:
SH
Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 94. What is the IUPAC name for the following compound?
SH
Ans: 5-methyl-2-heptanethiol Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Hard
95. What is the IUPAC name for the following compound? HO
SH
Ans: 5-mercapto-2-methyl-1-hexanol Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 96. What is the common name for the following compound? S
Ans: Methyl pentyl sulfide Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 97. What is the IUPAC name for the following compound? S
Ans: 2-ethylthiohexane Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Easy 98. Predict the product for the following reaction? NaSH
Br
Ans:
HS
Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium
99. Predict the product for the following reaction? CH2CH3
NaSH
H
OTs H3C
CH2CH3
Ans: HS
H CH3
Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 100. Predict the product for the following reaction? CH2CH3 H
CH3CH2SNa
Cl H3C
CH2CH3
Ans: H3CH2CS
H CH3
Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 101. Provide the reagents necessary to carry out the following conversion.
S
Br
Ans:
SNa
Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Easy
102. Predict the major product for the following reaction. NaIO4
S
Ans:
O S
Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 103. Predict the major product for the following reaction. S
NaIO4 O
O
O
S
I S
S
II
I
A) B) C) D) E)
III
I II III IV none of these Ans: A
Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 104. Predict the major product for the following reaction. S
2 H2O2
Ans:
O S O
S O
O
O
I
+ CH3CH2I IV
Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 105. Predict the major product for the following reaction. SH
NaOH/H2O/Br2
2
O
O S
S
S S
OH
IV
III
II
I
A) B) C) D) E)
S
Br
Br
I II III IV none of these Ans: D
Topic: Physical Properties Section: 14.3 Difficulty Level: Easy 106. Predict the major product for the following reaction. Zn /HCl
S S S S
I
A) B) C) D) E)
I II III IV II & IV Ans: D
SH Cl
Cl
S
II
SH
S
III
IV
Topic: Synthesis Section: 14.12 Difficulty Level: Medium 107. Provide a stepwise synthesis for the following. Br
Ans:
O
O
MgBr
Br
OH
1.
Mg/ether
PCC
2. H2O
O
Topic: Synthesis Section: 14.12 Difficulty Level: Hard 108. Provide a stepwise synthesis for the following. OH
+ enantiomer
Ans: Br
Br2
CH3CH2ONa
mBA
hν
O
+ enantiomer
Topic: Synthesis Section: 14.12 Difficulty Level: Hard
1. CH3CH3CH2MgBr 2. H2O
OH
+ enantiomer
109. Provide a stepwise synthesis for the following. OH
Ans:
O
1.
MgBr
mBA 2. H2O OH
Topic: Synthesis Section: 14.12 Difficulty Level: Hard 110. Provide a stepwise synthesis for the following.
O
Ans:
1. BH3
NaH
2. H2O2/NaOH/H2O ONa
OH
CH3CH2I O
Topic: Synthesis Section: 14.12 Difficulty Level: Medium
111. Provide a stepwise synthesis for the following.
Br O
Ans:
OH Br
H3O+
NaOH Br
Δ
O
dibutylether 1-propoxypropane 1-propoxyhexane dipropyl ether none of these Ans: D
Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 2. What is the common name for (CH3)2CHCH2OCH(CH3)2? A) B) C) D) E)
diisobutylether isobutyl isopropyl ether sec-butyl isopropyl ether diisopropylether none of these Ans: B
Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 3. What is the IUPAC name for CH3CH2CH2CH2OCH2CH3? A) B) C) D) E)
1-ethoxybutane 1-butoxyethane ethyl butyl ether 1-ethoxyhexane none of these Ans: A
Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Medium
4. What is the common name for the following compound? O
A) B) C) D) E)
1-butoxybutane sec-butyl isopropyl ether sec-butyl t-butyl ether n-butyl isopropyl ether none of these Ans: C
Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 5. A) B) C) D) E)
What is the IUPAC name for CH3CH2OCH2CH2CH2CH2OCH2CH3? 1,4-ethoxyoctane diethoxy butyl ether 1,2-diethoxymethane 1,2-diethoxyhexane 1,4-diethoxybutane Ans: E
Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 6. What is the correct structure for benzyl phenyl ether?
H3C
O
CH2OCH2
I
II
O
III
A) B) C) D) E)
I II III IV none of these Ans: D
CH3
CH2O
IV
Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 7. What is the correct structure for dibenzyl ether? O
CH2OCH2
I
II CH3
H3C
O
III
A) B) C) D) E)
CH3
CHOCH CH3 CH3
I II III IV none of these Ans: B
Topic: Nomenclature Section: 14.4 Difficulty Level: Hard 8. What is the IUPAC name for the following compound? O O
O
O
A) B) C) D) E)
15-crown-5 15-crown-4 5-crown-15 15-crown-15 none of these Ans: A
Topic: Nomenclature Section: 14.4 Difficulty Level: Hard
O
CH3CH2OCOCH2CH3 IV
OCH2CH3
9. What is the correct IUPAC name for the following compound?
A) B) C) D) E)
O
O
O
O
12-crown-5 12-crown-4 4-crown-12 12-crown-12 none of these Ans: B
Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 10. What is the IUPAC name for the following compound? O
Ans: 3-isopropoxy-2-methyloctane Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 11. What is the IUPAC name for the following compound? O
O
Ans: 1-ethoxy-1-methoxy-3-propylcyclohexane Topic: Nomenclature Section: 14.2 Difficulty Level: Medium
12. What is the IUPAC name for the following compound? O
Ans: E-4-isopropoxy-4,5-dimethylhex-2-ene Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 13. What is the IUPAC name for the following compound? CH3
CH3CH2OCOCH2CH3 OCH2CH3
Ans: 1,1,1-triethoxyethane Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 14. Provide the structure for (2S,5R)-5-ethoxy-2-octanol. OCH2CH3
Ans:
OH
Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 15. Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane. Ans:
O
OCH3 OCH3
Topic: Physical Properties Section: 14.3 Difficulty Level: Easy
16. A) B) C) D) E)
Which one of the following compounds will have the highest boiling point? CH3CH2CH2CH2CH3 CH3CH2CH2CH2OH CH3CH2CH2OCH3 CH3CH2CH2Cl CH3CH2OCH2CH3 Ans: B
Topic: Physical Properties Section: 14.3 Difficulty Level: Easy 17. A) B) C) D) E)
Which one of the following compounds will have the highest boiling point? CH3CH2CH2CH2CH3 CH3CH2CH2CH2OH CH3CH2CH2OCH3 CH3CH2CH2Cl CH3CH2OCH2CHOH Ans: E
Topic: Physical Properties Section: 14.3 Difficulty Level: Easy 18. A) B) C) D) E)
Which one of the following compounds will be least soluble in water? diethyl ether methyl propyl ether 1-butanol 2-butanol pentane Ans: E
Topic: Physical Properties Section: 14.3 Difficulty Level: Medium
19. Rank the following compounds in decreasing order of boiling points (highest to lowest)
A) B) C) D) E)
CH3CH2CH2CH2OH I II>IV>I>III I>IV>II>III IV>I>II>III III>II>I>IV IV>II>I>III Ans: C
CH3CH2OCH2CH3 II
CH3OCH3 III
HOCH2CH2CH2OH IV
Topic: Physical Properties Section: 14.3 Difficulty Level: Medium 20. Rank the following compounds in decreasing order of water solubility (highest to lowest) CH3CH2CH2CH2OH
A) B) C) D) E)
I
CH3CH2OCH2CH2CH3 II
CH3CH2OCH2CH2OH III
CH3CH2OH IV
II>IV>I>III I>IV>II>III IV>I>II>III III>II>I>IV IV>III>I>II Ans: E
Topic: Physical Properties Section: 14.3 Difficulty Level: Medium 21. Which one of the following compounds will have highest boiling point? O
O
HO
Ans: III
I
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Easy
II
O
OH
HO
III
HO
IV
22. Predict the product for the following reaction. H2SO4 2 CH3CH2CH2OH 1400C A) propene B) Diethyl ether C) 1-hexanol D) 1-propoxypropane Ans: D Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 23. Predict the product for the following reaction. H2SO4 2-cyclopentylethanol 1400C O Ans:
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 24. Provide a curved arrow mechanism for the formation of the product. O
H2SO4
O HO
OH O
Ans: O HO
O
OH
HO
O H
O
S
OH2
+
OH
O
O
+ H2SO4 O O O
S
H O
OH
O
S O
O
O
O OH
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 25. 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 26. Which one of the following reactions would produce t-butyl methyl ether in high yield? A) B) C) D)
t-butyl chloride + sodium methoxide t-butanol + methanol in presence of H2SO4 at 140°C t-butyl bromide + bromomethane in presence of NaOH Sodium t-butoxide + bromomethane Ans: D
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 27. Which one of the following reactions would produce t-butyl methyl ether in high yield? A) B) C) D)
CH3ONa + (CH3)3CBr CH3OH + (CH3)3COH in presence of H2SO4 at 140°C CH3Cl + (CH3)3CBr in presence of NaOH (CH3)3CONa + CH3Br Ans: D
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium
28. 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 29. Predict the product for the following reaction. OH
1. NaH 2. CH3CH2CH2I
Ans:
OCH2CH2CH3
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 30. Provide the reagents necessary to carry out the following conversion. OH
Ans:
1. PBr3 2. ONa
O
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Hard 31. Predict the product for the following reaction. OH Br
NaOH heat
Ans: O
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 32. Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis. O
Ans:
ONa
+ CH3CH2CH2Cl
Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 33. Provide the reagents necessary to prepare the following compound using Williamson synthesis. (CH3)2CHCH2OCH(CH3)2 Ans: (CH3)2CHCH2Cl + (CH3)2CHONa Topic: Preparation of ethers Section: 14.5 Difficulty Level: Hard
34. Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product. NaOH Br
OH
Ans:
O
Mechanism H Br
O
OH
+ NaBr O
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Medium 35. Predict the product for the following reaction. 3-methyl-2-pentene
A) B) C) D) E)
1. Hg(OAc)2, CH3CH2OH 2. NaBH4
3-methyl-3-pentanol 3-ethoxy-3-methylpentane 3-methyl-2-pentanol 2-ethoxy-3-methylpentane 1-ethoxy-3-methylpentane Ans: B
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard
Br
O
Na
36. Predict the product for the following reaction. 1-ethyl-1-cyclohexene
A) B) C) D) E)
1. Hg(OAc)2, CH3CH2OH 2. NaBH4
1-ethyl-1-cyclohexanol 2-ethoxy-1-ethylcyclohexane 1-ethoxy-1-ethylcyclohexane 2-ethoxy-3-ethylcyclohexane 1-ethoxy-2-ethylcyclohexane Ans: C
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 37. Predict the product for the following reaction. 1. Hg(OAc)2, CH3OH 2. NaBH4
A) B) C) D) E)
2-methyl-1-hexanol 2-methoxy-2-methylhexane 1-methoxy-2-methylhexane 2-methoxy-3-methylhexane 2-methyl-2-hexanol Ans: B
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 38. Predict the product for the following reaction.
1. Hg(OAc)2, 2. NaBH4
Ans: O
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard
OH
39. Predict the product for the following reaction. . 1. Hg(OAc)2, CH3CH2OH 2. NaBH4
Ans: O
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 40. Provide the reagents necessary to prepare the following compound using . alkoxymercuration-demercuration. O
OH
Ans: 1. Hg(OAc)2, 2. NaBH4
Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 41. Provide the reagents necessary to carry out the following conversion. . OC(CH3)3
Ans:
1. Hg(OAc)2, (CH3)3COH 2. NaBH4
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Easy
42. Predict the product(s) for the following reaction. HBr
O
A) B) C) D) E)
excess
ethanol + 1-bromopropane 1-propanol + 1-bromoethane 1-propanol + ethanol 1-bromopropane + 1-bromoethane none of these Ans: D
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Easy 43. Predict the product(s) for the following reaction. O
HI excess
A) B) C) D) E)
ethanol + phenol phenol + 1-iodoethane iodobenzene + ethanol iodobenzene + 1-iodoethane none of these Ans: B
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium
44. Predict the product(s) for the following reaction. HBr O
excess
CH2OH
Br
+
III
II
I OH
OCH2Br
I II III IV V Ans: C
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium
CH2Br
OH
+
+
A) B) C) D) E)
CH2OH
OH
CH2Br
Br
+
+
IV
V
45. Predict the product(s) for the following reaction. HI excess
O
I
O
I
I
I
OH
III
II
OH
+
I
O
A) B) C) D) E)
I
V
IV
I II III IV V Ans: B
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 46. Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product. HBr excess
O
Br
Ans: Br
Mechanism
O
O H
Br
H
Br
H
Br Br
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard
Br
OH
+ H2O
Br
OH2
Br
Br
47. Predict the product(s) for the following reaction. O
HI excess O
Ans:
I
2 I
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard 48. Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product. HBr excess
O
Ans: Br
OH
Mechanism Br O
O H
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard
Br
Br H
OH
49. Predict the product(s) for the following reaction. HI O
1 mol
Ans:
OH I
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 50. Predict the product(s) for the following reaction. O
HBr excess
Ans: Br
+ Br
Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 51. 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
52. What is the IUPAC name for the following compound? O
A) B) C) D) E)
2-ethyl-1-methyloxirane 1-ethyl-2-methyloxirane 2-ethyl-1-methyloxypentane 1-ethyl-2-methyloxypentane none of these Ans: B
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 53. What is the IUPAC name for the following compound? O
A) B) C) D) E)
2-ethyl-1-isopropyl-2-methyloxirane 1-ethyl-2-isopropyl-1-methyloxirane 2,4-dimethyloxyhexane 1-ethyl-2,4-dimethyloxyhexane none of these Ans: B
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 54. Provide the structure for tetrahydrofuran. Ans: O
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium
55. Provide the structure for oxetane. Ans:
O
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 56. Provide the IUPAC name for the following compound. O
Ans: (1S, 2S)-1-ethyl-2-isopropyloxirane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 57. Provide the IUPAC name for the following compound. O
Ans: (1S, 2R)-1-ethyl-2-phenyloxirane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 58. Provide the common name for the following compound. O
O
Ans: 1,4-dioxane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium
59. Provide the IUPAC name for the following compound.
O
Ans: (1S,2R)-1-methyl-1,2-epoxycyclohexane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 60. Provide the structure for (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane. Ans:
O
Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 61. Provide the structure for 1,1,2-trimethyl-2-phenyloxirane. Ans: O
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium
62. Predict the product for the following reaction. (E)-2-pentene + mBA O
I
A) B) C) D)
O
II O
O
III
IV
I II III IV Ans: D
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 63. Predict the product for the following reaction. (Z)-3-hexene + mBA O
I
A) B) C) D)
O
II O
O
III
IV
I II III IV Ans: A
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium
64. Predict the product for the following reaction. O
+ CH3COOH
OH
OH
A) B) C) D)
I II III IV Ans: C
O O
III
II
I
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 65. Predict the product for the following reaction. 1-methylcyclohexene + mBA Ans: O
+ enantiomer
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 66. Provide the reagents necessary to carry out the following conversion. O
Ans: mBA
O
+ enantiomer IV
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 67. Predict the product for the following reaction. 1. Br2/H2O 2. NaOH Br
Br
OH Br
OH
A) B) C) D)
I II III IV Ans: D
II
I
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 68. Predict the product for the following reaction. 1. Br2/H2O 2. NaOH
Ans:
O
+ enantiomer
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium
O
III
IV
69. Provide the structure(s) of the product(s) in the following reaction sequence. Br2/H2O
A
NaOH
B
Ans: OH
+ enantiomer
O
Br
B
A
Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 70. Predict the product for the following reaction. O H
CH3 OOH
+ H
Cl
Ans: O H
CH3
+ enantiomer H
Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium
+ enantiomer
71. Predict the product for the following reaction. (CH3)3COOH OH
Ti[OCH(CH3)2]4 (+) DET OH
Ans:
O
Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium 72. Predict the product for the following reaction. OH
(CH3)3COOH Ti[OCH(CH3)2]4 (+) DET
Ans:
OH
O
Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium
73. Predict the product for the following reaction. OH
(CH3)3COOH Ti[OCH(CH3)2]4 (-) DET
OH
Ans:
O
Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium 74. Predict the product for the following reaction. HO
(CH3)3COOH Ti[OCH(CH3)2]4 (-) DET
Ans: HO
O
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy
75. Predict the product(s) for the following reaction. O
H3O+
OH
OH
H O
OH
A) B) C) D) E)
OH
OH
+ enantiomer
II
I
IV
III
I II III IV none of these Ans: C
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy 76. Predict the product(s) for the following reaction. O
HBr
H OH
Br
Br
O
Br
A) B) C) D) E)
I
HO
I II III IV none of these Ans: A
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy
II
III
Br
IV
77. Predict the product(s) for the following reaction. O
CH3OH/H2SO4
OCH3
H
HO
OH
I
A) B) C) D) E)
H
H3CO
OH
OCH3
HO
H3CO
II
IV
III
I II III IV none of these Ans: B
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 78. Predict the product(s) for the following reaction. O
CH3OH/H2SO4
OCH3
OH
OCH3
I
A) B) C) D) E)
I II III IV none of these Ans: A
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium
OCH3
OCH3
OH
II
OH
III
OH
Iv
79. Predict the product(s) for the following reaction.
O
CH3CH2OH/H2SO4
I
A) B) C) D) E)
OCH2CH3 CH3
OH
CH3 OH
CH3
OCH2CH3
OCH2CH3
OCH2CH3 CH3
OH
III
II
OH
IV
I II III IV none of these Ans: C
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 80. Provide the reagents necessary to carry out the following conversion. OH
O
Cl
Ans: HCl Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 81. Provide the reagents necessary to carry out the following conversion. H3C
O
CH3 H3CO
OH H
Ans: CH3OH/H2SO4
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 82. Predict the product(s) for the following reaction. O
1. NaSH 2. H2O
HO
H
HS
H
SH
I
A) B) C) D) E)
I II III IV none of these Ans: A
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy
NaO
HO
OH
II
OH
OH
III
IV
83. Predict the product(s) for the following reaction. O
1. NaCN 2. H2O OH
OH
I
II
+ enantiomer
CN
OH
OH
+ enantiomer
A) B) C) D) E)
CN
CN
CN
+ enantiomer III
IV
I II III IV none of these Ans: C
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy 84. Predict the product(s) for the following reaction.
O
1. CH3ONa 2. H2O
I
A) B) C) D) E)
OCH3
OH
CH3 OH
CH3
CH3
OCH3
OCH3
OH
I II III IV none of these Ans: D
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium
II
III
CH3 OH
OCH3
IV
85. Predict the product(s) for the following reaction. O
1. CH3MgBr 2. H2O OH
Ans:
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 86. Predict the product(s) for the following reaction. H3C
O
1. (CH3)2NH 2. H2O
Ans:
H3C
OH N(CH3)2
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium
87. Provide the reagents necessary to carry out the following conversion. CH3 OH
+ enantiomer CH3
Ans:
1. mBA 2. CH3MgBr 3. H2O
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 88. Provide the reagents necessary to carry out the following conversion.
O
Ans:
OH
1. LiAlH4 2. H2O
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 89. Provide the reagents necessary to carry out the following conversion. OH
NH2
Ans:
1. mBA 2. NH3
Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard
+ enatiomer
90. Provide the reagents necessary to carry out the following conversion. OH
O
Ans:
MgBr
1. 2. H2O Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 91. Provide a stepwise curved arrow mechanism for the following reaction. OH
O
H3O+ heat
OH H
Ans: O
O H
O
H
+ H2O
H OH
OH
H2O
H2O O H
OH
+ H3O+
OH
H
Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Easy 92. What is the correct structure for 3-methyl-1-hexanethiol? Ans: HS
Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 93. What is the correct structure for phenylthiol? Ans:
SH
Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 94. What is the IUPAC name for the following compound?
SH
Ans: 5-methyl-2-heptanethiol Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Hard
95. What is the IUPAC name for the following compound? HO
SH
Ans: 5-mercapto-2-methyl-1-hexanol Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 96. What is the common name for the following compound? S
Ans: Methyl pentyl sulfide Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 97. What is the IUPAC name for the following compound? S
Ans: 2-ethylthiohexane Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Easy 98. Predict the product for the following reaction? NaSH
Br
Ans:
HS
Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium
99. Predict the product for the following reaction? CH2CH3
NaSH
H
OTs H3C
CH2CH3
Ans: HS
H CH3
Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 100. Predict the product for the following reaction? CH2CH3 H
CH3CH2SNa
Cl H3C
CH2CH3
Ans: H3CH2CS
H CH3
Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 101. Provide the reagents necessary to carry out the following conversion.
S
Br
Ans:
SNa
Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Easy
102. Predict the major product for the following reaction. NaIO4
S
Ans:
O S
Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 103. Predict the major product for the following reaction. S
NaIO4 O
O
O
S
I S
S
II
I
A) B) C) D) E)
III
I II III IV none of these Ans: A
Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 104. Predict the major product for the following reaction. S
2 H2O2
Ans:
O S O
S O
O
O
I
+ CH3CH2I IV
Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 105. Predict the major product for the following reaction. SH
NaOH/H2O/Br2
2
O
O S
S
S S
OH
IV
III
II
I
A) B) C) D) E)
S
Br
Br
I II III IV none of these Ans: D
Topic: Physical Properties Section: 14.3 Difficulty Level: Easy 106. Predict the major product for the following reaction. Zn /HCl
S S S S
I
A) B) C) D) E)
I II III IV II & IV Ans: D
SH Cl
Cl
S
II
SH
S
III
IV
Topic: Synthesis Section: 14.12 Difficulty Level: Medium 107. Provide a stepwise synthesis for the following. Br
Ans:
O
O
MgBr
Br
OH
1.
Mg/ether
PCC
2. H2O
O
Topic: Synthesis Section: 14.12 Difficulty Level: Hard 108. Provide a stepwise synthesis for the following. OH
+ enantiomer
Ans: Br
Br2
CH3CH2ONa
mBA
hν
O
+ enantiomer
Topic: Synthesis Section: 14.12 Difficulty Level: Hard
1. CH3CH3CH2MgBr 2. H2O
OH
+ enantiomer
109. Provide a stepwise synthesis for the following. OH
Ans:
O
1.
MgBr
mBA 2. H2O OH
Topic: Synthesis Section: 14.12 Difficulty Level: Hard 110. Provide a stepwise synthesis for the following.
O
Ans:
1. BH3
NaH
2. H2O2/NaOH/H2O ONa
OH
CH3CH2I O
Topic: Synthesis Section: 14.12 Difficulty Level: Medium
111. Provide a stepwise synthesis for the following.
Br O
Ans:
OH Br
H3O+
NaOH Br
Δ
O
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