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Test Bank for Organic Chemistry 2nd Edition by Klein E all of these Ans: E Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 2.. Ans: Topic: Preparation of Ethers Sectio

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Test Bank for Organic Chemistry 2nd Edition by Klein

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

Section: 14.2

3 What is the common name for (CH3)2CHCH2OCH(CH3)2?

A) Diisobutylether

B) isobutyl isopropyl ether

C) sec-butyl isopropyl ether

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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

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

6 What is the IUPAC name for CH3CH2OCH2CH2CH2CH2OCH2CH3? A) 1,4-ethoxyoctane

B) diethoxy butyl ether

7 What is the correct structure for benzyl phenyl ether?

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Ans: D

Topic: Nomenclature

Section: 14.2

8 What is the correct structure for dibenzyl ether?

9 What is the IUPAC name for the following compound? Ans: 3-isopropoxy-2-methyloctane

Topic: Nomenclature

Section: 14.2

10 What is the IUPAC name for the following compound? Ans: 1-ethoxy-1-methoxy-3-propylcyclohexane

Topic: Nomenclature

Section: 14.2

11 What is the IUPAC name for the following compound? Ans: E-4-isopropoxy-4,5-dimethylhex-2-ene

Topic: Nomenclature

Section: 14.2

12 What is the IUPAC name for the following compound?

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Ans: (1S,3S)-1-ethoxy-3-methylcyclohexane

Topic: Nomenclature

Section: 14.2

Difficulty Level: Hard

Ans: 1,1,1-triethoxyethane

Topic: Nomenclature

Section: 14.2

14 Provide the structure for 2-iodo-4-isopropyl-1-methoxybenzene Ans:

Topic: Nomenclature

Section: 14.2

15 Provide an IUPAC name for the following compound

Ans: 4-t-butyl-1-ethoxy-2-methylbenzene

Topic: Nomenclature

Section: 14.2

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

Topic: Nomenclature

Section: 14.2

17 Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane Ans: Topic: Nomenclature

Section: 14.2

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

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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

20 Which one of the following compounds will have the highest boiling point? A) CH3CH2CH2CH2CH3

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

22 Which one of the following compounds will be least soluble in water?

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23 Rank the following compounds in decreasing order of boiling points (highest to lowest)

24 Rank the following compounds in decreasing order of water solubility (highest

25 Which one of the following compounds has highest boiling point?

Ans: III

Topic: Crown ethers

Section: 14.4

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

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Section: 14.4

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

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

Topic: Crown ethers

Section: 14.4

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

Topic: Crown ethers

Section: 14.4

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

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Topic: Crown ethers

Section: 14.4

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

Topic: Crown ethers

Section: 14.4

32 Identify the missing reagent needed to carry out the following transformation A) 12-crown-5

33 Identify the missing reagent needed to carry out the following transformation Ans: 18-crown-6

Topic: Crown ethers

Section: 14.4

34 Identify the missing reagent needed to carry out the following transformation Ans: 18-crown-6

Topic: Preparation of ethers

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Section: 14.5

35 Predict the product for the following reaction

Ans:

Topic: Preparation of Ethers

Section: 14.5

37 Provide a curved arrow mechanism for the formation of the product

Ans:

Section: 14.5

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

Section: 14.5

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

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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

Section: 14.5

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

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

Section: 14.5

Ans:

Section: 14.5

43 Provide the reagents necessary to carry out the following conversion

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Ans: 1 PBr3

2

Section: 14.5

Ans:

Section: 14.5

45 Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis Ans:

Section: 14.5

46 Provide the reagents necessary to prepare the following compound using Williamson ether synthesis Ans:

Section: 14.5

47 Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product

Ans:

Mechanism

Section: 14.5

A) 3-methyl-3-pentanol

B) 3-ethoxy-3-methylpentane

C) 3-methyl-2-pentanol

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D) 2-ethoxy-3-methylpentane

E) 1-ethoxy-3-methylpentane Ans: B

Section: 14.5

49 Predict the product for the following reaction A) 1-ethyl-1-cyclohexanol

50 Predict the product for the following reaction A) 2-methyl-1-hexanol

51 Predict the product for the following reaction Ans:

Section: 14.5

52 Predict the product for the following reaction Ans: Topic: Preparation of Ethers

Section: 14.5

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

54 Provide the reagents necessary to carry out the following conversion Ans: Topic: Reactions of Ethers

Section: 14.6

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

Topic: Reactions of Ethers

Section: 14.6

A) ethanol + phenol

B) phenol + iodoethane

C) iodobenzene + ethanol

D) iodobenzene + iodoethane

Section: 14.6

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59 Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product

Ans:

Mechanism

Section: 14.6

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61 Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product

Ans:

Mechanism

Section: 14.6

Ans:

Section: 14.6

Ans:

Section: 14.6

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

A) 3-ethyl-2-methyloxirane

B) 2-ethyl-3-methyloxirane

C) 2-ethyl-1-methyloxypentane

D) 1-ethyl-2-methyloxypentane

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Section: 14.7

66 What is the IUPAC name for the following compound? A) 2-ethyl-3-isopropyl-2-methyloxirane

67 Provide the structure for tetrahydrofuran Ans:

Section: 14.7

68 Provide the structure for oxetane Ans:

Section: 14.7

69 Provide the IUPAC name for the following compound Ans: (2S, 3S)-2-ethyl-3-isopropyloxirane

Section: 14.7

70 Provide the IUPAC name for the following compound Ans: (2S, 3R)-2-ethyl-3-phenyloxirane

Section: 14.7

71 Provide the common name for the following compound

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Ans: 1,4-dioxane

Section: 14.7

72 Provide the IUPAC name for the following compound

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

Section: 14.7

73 Provide the structure for (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane Ans: Topic: Nomenclature of epoxides

Section: 14.7

74 Provide the structure for (R)-2,2,3-trimethyl-3-phenyloxirane Ans:

Topic: Preparation of epoxides

Section: 14.8

75 Predict the product for the following reaction (E)-2-pentene + mCPBA

76 Predict the product for the following reaction (Z)-3-hexene

+ mCPBA

A) I

B) II

C) III

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D) IV

Ans: A

Section: 14.8

1-methylcyclohexene + mCPBA Ans:

Section: 14.8

79 Provide the reagents necessary to carry out the following conversion Ans: mCPBA

Section: 14.8

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Ans:

Section: 14.8

82 Provide the structure(s) of the product(s) in the following reaction sequence Ans:

Section: 14.8

Ans:

Section: 14.8

84 Provide the reactants necessary to prepare the following compound

Ans:

Section: 14.8

Ans:

Section: 14.8

Ans:

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Section: 14.9

Topic: Reactions of epoxides

Section: 14.10

91 Predict the product(s) for the following reaction A) I

B) II

C) III

D) IV

Topic: Reactions of epoxides

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