Chapter_Fourteen_Topic_Nomenclature_of_E.pdf

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 structure for benzyl phenyl ether? O

CH2OCH2

II

I

H3C

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 structure for dibenzyl ether? ether? O

CH2OCH2

II

I

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 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 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 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

CH3CH2OCH2CH3

CH3OCH3

I

II

III

HOCH2CH2CH2OH IV

II>IV>I>III I>IV>II>III IV>I>II>III III>II>I>IV IV>II>I>III Ans: C

Topic: Physical Properties Section: 14.3 Difficulty Level: Medium 20. Rank the following compounds in decreasing order of water solubility (highest to lowest) CH3CH2CH2CH2OH

II

I

A) B) C) D) E)

CH3CH2OCH2CH2CH3

CH3CH2OCH2CH2OH

CH3CH2OH IV

III

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

O

OH

HO

I

Ans: III Topic: Preparation of ethers Section: 14.5 Difficulty Level: Easy

II

III

HO

IV

22. Predict the product for the following reaction. H2SO4 2 CH3CH2CH2OH

A) B) C) D)

0

140 C

propene Diethyl ether 1-hexanol 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 0 140 C 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. PBr 3 2. ONa

O

Topic: Preparation of ethers Section: 14.5 Difficulty Level: Hard 31. Predict the product for the following reaction. OH

NaOH

Br

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

ONa

Ans:

+ 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

echanism H r

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. OH

1. Hg(OAc)2, 2. NaBH4

Ans: O

Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard

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

CH2Br

OH

+

+

+

I

II

III

OH

OCH2Br

A) B) C) D) E)

CH2OH

OH

I II III IV V Ans: C

Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium

CH2Br

Br

+

+

IV

V

45. Predict the product(s) for the following reaction. HI excess

O

I

O

I

I

I

OH

III

II

+

I

OH

O

V

IV

A) B) C) D) E)

I

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

Br

H

H

Br Br

Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard

OH2

OH

Br H

Br

Br

O

O

+ H2O

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

OH

Br H

Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard

Br

H

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 + mCPBA O

I

O

II O

O

III

A) B) C) D)

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 + mCPBA O

O

I

II O

III

A) B) C) D)

I II III IV Ans: A


O

IV

64. Predict the product for the following reaction. O

+

CH3COOH

OH O

OH

O

A) B) C) D)

III

II

I

I II III IV Ans: C

Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 65. Predict the product for the following reaction. 1-methylcyclohexene + mCPBA 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: mCPBA

O

+ enantiomer IV

Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 67. Predict the product for the following reaction. 1. Br 2/H2O 2. NaOH Br Br

OH

Br

OH

II

I

A) B) C) D)

I II III IV Ans: D

Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 68. Predict the product for the following reaction. 1. Br 2/H2O 2. NaOH

Ans: O

+ enantiomer


O

III

IV

69. Provide the structure(s) of the product(s) in the following reaction sequence. Br 2/H2O

NaOH A

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


+ 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


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


H3O

+

OH

OH

H O

OH

OH

OH

+ enantiomer II

I

A) B) C) D) E)

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

I

A) B) C) D) E)

HO

I II III IV none of these Ans: A


II

III

Br

IV


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)


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

OH

OCH2CH3

I

A) B) C) D) E)

OCH2CH3

OCH2CH3

CH3

CH3

CH3

OCH2CH3

OH

OH

OH

CH3

III

II

IV


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

OH

H3 CO 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)



NaO

HO

OH

II

OH

OH

III

IV


1. NaCN 2. H2O OH

OH

+ enantiomer

+ enantiomer

IV

III

II

I

CN

OH

OH

+ enantiomer

A) B) C) D) E)

CN

CN

CN


Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy 84. Predict the product(s) for the following reaction.

O

1. CH3ONa 2. H2O

OH

OCH3

I

A) B) C) D) E)

OCH3

OH

CH3



II

CH3

CH3

CH3

OH

OCH3

OH

OCH3

III

IV


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)2 NH 2. H2O

Ans:

H3C

OH N(CH3)2


87. Provide the reagents necessary to carry out the following conversion. CH3 OH

+ enantiomer

CH3

Ans:

1. mCPBA 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. OH O

Ans:

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. mCPBA 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?

Br

Ans:

NaSH

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

CH3CH2SNa

H

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.

S

NaIO4

O

Ans:

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

O I

S

S

S

S I

O

O

+ CH3CH2I II

I

A) B) C) D) E)

III


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

IV

Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 105. Predict the major product for the following reaction. SH

NaOH/H2O/Br 2

2

O

O S

S Br

S S

OH

IV

III

II

I

A) B) C) D) E)

S Br


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

Br 2

CH3CH2ONa

mCPBA

h!

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 mCPBA 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/H 2O ONa

OH

CH3CH2I

O

Topic: Synthesis Section: 14.12 Difficulty Level: Medium

Chapter_Fourteen_Topic_Nomenclature_of_E.pdf

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