ch14 final tb klein1e - chemconnections

Chapter Fourteen Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy

1. 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

2. 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

3. 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

4. What is the common name for the following compound? O

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

5. 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

6. What is the correct structure for benzyl phenyl ether?

O CH2OCH2

H3C O CH3 CH2O

I II

III IV

A) I B) II C) III D) IV E) none of these

Ans: D

Topic: Nomenclature Section: 14.2 Difficulty Level: Medium

7. What is the correct structure for dibenzyl ether?

O CH2OCH2

H3C O CH3 CHOCH

CH3 CH3

I II

III IV

CH3CH2OCOCH2CH3

CH3

OCH2CH3


Ans: B Topic: Nomenclature Section: 14.4 Difficulty Level: Hard

8. What is the IUPAC name for the following compound?

O

O

O

OO

A) 15-crown-5 B) 15-crown-4 C) 5-crown-15 D) 15-crown-15 E) none of these

Ans: A Topic: Nomenclature Section: 14.4 Difficulty Level: Hard

9. What is the correct IUPAC name for the following compound?

O O

OO

A) 12-crown-5 B) 12-crown-4 C) 4-crown-12 D) 12-crown-12 E) 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



O O

Ans: 1-ethoxy-1-methoxy-3-propylcyclohexane



Ans: E-4-isopropoxy-4,5-dimethylhex-2-ene

Topic: Nomenclature Section: 14.2 Difficulty Level: Hard


CH3CH2OCOCH2CH3

CH3

OCH2CH3 Ans: 1,1,1-triethoxyethane


14. Provide the structure for (2S,5R)-5-ethoxy-2-octanol. Ans:

OH

OCH2CH3


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. 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

17. 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

18. 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

19. Rank the following compounds in decreasing order of boiling points (highest to lowest) CH3CH2CH2CH2OH CH3CH2OCH2CH3 CH3OCH3 HOCH2CH2CH2OH

I II III IV 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

20. Rank the following compounds in decreasing order of water solubility (highest to lowest) CH3CH2CH2CH2OH CH3CH2OCH2CH2CH3 CH3CH2OHCH3CH2OCH2CH2OH

I II IVIII 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

21. Which one of the following compounds will have highest boiling point?

HO

O O O

HO

OH

I II III HO IV Ans: III

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

22. Predict the product for the following reaction.

2 CH3CH2CH2OH

H2SO4

1400C

A) propene B) Diethyl ether C) 1-hexanol D) 1-propoxypropane

Ans: D Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium


2-cyclopentylethanol

H2SO41400C

Ans: O

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

24. Provide a curved arrow mechanism for the formation of the product.

HOO

OHH2SO4

O

O

Ans:

HOO

OH

H O S

O

O

OH

HOO

OH2

O S

O

O

OH+

O

O

HO S

O

O

OHO

O

+ H2SO4

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.


26. 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


27. 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


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


30. Provide the reagents necessary to carry out the following conversion.

OH O

Ans: 1. PBr3 2.

ONa

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

31. Predict the product for the following reaction. Br

OH 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


33. Provide the reagents necessary to prepare the following compound using Williamson synthesis. (CH3)2CHCH2OCH(CH3)2

Ans: + (CH3)2CHONa(CH3)2CHCH2Cl

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.

Br OH

NaOH

Ans:

O Mechanism

Br OH

OH Br O Na

O

+ NaBr

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

35. Predict the product for the following reaction. 1. Hg(OAc)2, CH3CH2OH

2. NaBH43-methyl-2-pentene

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

36. Predict the product for the following reaction. 1. Hg(OAc)2, CH3CH2OH

2. NaBH41-ethyl-1-cyclohexene

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

37. Predict the product for the following reaction. 1. Hg(OAc)2, CH3OH

2. NaBH4

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


1. Hg(OAc)2,

2. NaBH4

OH

Ans:

O


39. .

Predict the product for the following reaction.

1. Hg(OAc)2, CH3CH2OH

2. NaBH4 Ans:

O


40. .

Provide the reagents necessary to prepare the following compound using alkoxymercuration-demercuration.

O

Ans:

1. Hg(OAc)2,

2. NaBH4

OH


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.

O

HBr

excess A) ethanol + 1-bromopropane B) 1-propanol + 1-bromoethane C) 1-propanol + ethanol D) 1-bromopropane + 1-bromoethane E) none of these

Ans: D Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Easy

43. Predict the product(s) for the following reaction. HI

excess

O

A) ethanol + phenol B) phenol + 1-iodoethane C) iodobenzene + ethanol D) iodobenzene + 1-iodoethane E) none of these

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


HBr

excessO

Br CH2OH

I

OH CH2OH

II

OH CH2Br

III

+ + +

OCH2Br OH

IV

Br CH2Br

V

+ +

A) I B) II C) III D) IV E) V

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


HI

excessO

O I I I OH

I II III

OH I

IVO I

V

+

A) I B) II C) III D) IV E) 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

excessO

Ans:

BrBr

Mechanism

O

H Br

O

HBr

OHBr

H Br

OH2Br

Br

BrBr

+ H2O

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


HI

excessO

O

Ans:

II

2 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.

O

HBr

excess

Ans:

Br

OH Mechanism

BrO

H Br

O

H

OH

Br

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


HI

1 molO

Ans:

IOH

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


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


A) 2-ethyl-1-methyloxirane B) 1-ethyl-2-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


A) 2-ethyl-1-isopropyl-2-methyloxirane B) 1-ethyl-2-isopropyl-1-methyloxirane C) 2,4-dimethyloxyhexane D) 1-ethyl-2,4-dimethyloxyhexane E) 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


57. Provide the IUPAC name for the following compound. O

Ans: (1S, 2R)-1-ethyl-2-phenyloxirane


58. Provide the common name for the following compound.

O

O

Ans: 1,4-dioxane


59. Provide the IUPAC name for the following compound.

O

Ans: (1S,2R)-1-methyl-1,2-epoxycyclohexane


60. Provide the structure for (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane. Ans:

O


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 O

I II OO

III IV A) I B) II C) III D) 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 OO

III IV A) I B) II C) III D) IV

Ans: A Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium


CH3COOH

O

+

OH O

OHO

O

I II III IV

+ enantiomer

A) I B) II C) III D) 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


66. Provide the reagents necessary to carry out the following conversion. O

Ans:

mCPBA



1. Br2/H2O

2. NaOH

OH

BrBr

Br

OHO

I II III IV

A) I B) II C) III D) IV

Ans: D Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium


1. Br2/H2O

2. NaOH

Ans:

O

+ enantiomer


69. Provide the structure(s) of the product(s) in the following reaction sequence.

Br2/H2OA B

NaOH

Ans:

OH

Br

O

A B

+ enantiomer + enantiomer



H CH3

H

+OOH

O

Cl Ans:

O

H CH3

H+ enantiomer



OH

(CH3)3COOH

Ti[OCH(CH3)2]4(+) DET

Ans:

O

OH



(CH3)3COOH

Ti[OCH(CH3)2]4(+) DET

OH

Ans: OH

O


73. Predict the product for the following reaction. (CH3)3COOH

Ti[OCH(CH3)2]4(-) DET

OH

Ans:

O

OH


74. Predict the product for the following reaction. (CH3)3COOH

Ti[OCH(CH3)2]4(-) DET

HO

Ans:

OHO

Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy


OH3O

+

OH OH

OH

OH

OH

O

H

I II IIIIV+ enantiomer


Ans: C Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy


OHBr

O

H

Br

OH

HO

Br

Br

Br

I II III IV


Ans: A Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy


OCH3OH/H2SO4

OCH3

HHO

OH

HH3CO

OCH3

H3CO

OH

HO

I II IIIIV


Ans: B Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium


CH3OH/H2SO4

O

OH

OCH3

OCH3

OCH3

OH

OH

OCH3

OH

I II III Iv


Ans: A Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium


CH3CH2OH/H2SO4O

I II III IV

OHCH3

OCH2CH3

CH3

OH

OCH2CH3

CH3

OCH2CH3

OH

CH3

OCH2CH3

OH


Ans: C Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium


OH

Cl

O

Ans: HCl Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium


OH3C CH3H3CO

OH

H

Ans: CH3OH/H2SO4

Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium


O1. NaSH

2. H2O

SH

HHO

OH

HHS

OH

HO

OH

NaO

I II IIIIV


Ans: A Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy


O1. NaCN

2. H2O

OH

OH

OH

CN

OH

CN CN

CN

I II III IV+ enantiomer + enantiomer + enantiomer


Ans: C Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy


1. CH3ONaO

2. H2O

I II III

OHCH3

OCH3

CH3

OH

OCH3

CH3

OCH3

OH

OHCH3

OCH3IV


Ans: D Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium


1. CH3MgBr

2. H2O

O

Ans: OH



OH3C

(CH3)2NH

H2O

1.

2.

Ans: OHH3C N(CH3)2



CH3

CH3

OH

+ enantiomer

Ans: 1. mCPBA 2. CH3MgBr 3. H2O

Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard


OHO

Ans: 1. LiAlH4 2. H2O



OH

NH2 + enatiomer

Ans: 1. mCPBA 2. NH3



O

OH

Ans:

1.

MgBr

2. H2O


91. Provide a stepwise curved arrow mechanism for the following reaction. O

H3O+

heat

OH

OH

Ans: O

OH

H O H

H

H2O

O

H

OH

O

HH

H2O

+ H2O

+ H3O+

OH

OH

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


SH

Ans: 5-methyl-2-heptanethiol Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Hard


SH

HO

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 NaSH

Ans: HS

Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium


NaSHOTsH

H3C

CH2CH3

Ans:

HS H

CH2CH3

CH3 Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium


ClH

H3C

CH2CH3

CH3CH2SNa

Ans:

H3CH2CS H

CH2CH3

CH3 Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium


Br S

Ans: SNa

Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Easy

102. Predict the major product for the following reaction. S NaIO4

Ans:

S

O

Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium

103. Predict the major product for the following reaction.

NaIO4

S

S

O

S

O

O

SI

O

O

SI

O

+ CH3CH2II II III IV


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:

S

O

O

Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium

105. Predict the major product for the following reaction. SH

NaOH/H2O/Br22

SS

SBr

S

O

OHS

O

Br

I II III IV


Ans: D Topic: Physical Properties Section: 14.3 Difficulty Level: Easy

106. Predict the major product for the following reaction. Zn /HCl

SS

SSH

SCl

SHSS

Cl

I II III IV

A) I B) II C) III D) IV E) II & IV

Ans: D

Topic: Synthesis Section: 14.12 Difficulty Level: Medium

107. Provide a stepwise synthesis for the following. Br O

Ans: Br

Mg/ether

MgBr O

1.

2. H2O

OH

PCC

O

Topic: Synthesis Section: 14.12 Difficulty Level: Hard

108. Provide a stepwise synthesis for the following.

OH

+ enantiomer

Ans:

O

Br CH3CH2ONa

OH

hν

mCPBA

1. CH3CH3CH2MgBr

2. H2O

Br2

+ enantiomer+ enantiomer


109. Provide a stepwise synthesis for the following. OH

Ans: OMgBr

OH

mCPBA

1.

2. H2O



O

Ans:

CH3CH2I

OH

NaH

O

ONa

1. BH3

2. H2O2/NaOH/H2O

Topic: Synthesis Section: 14.12 Difficulty Level: Medium


O

Br

Ans:

Δ

NaOH

O

H3O+Br

Br

OH

ch14 final tb klein1e - chemconnections

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