test bank for organic chemistry 2nd edition by klein · pdf filetest bank for organic...

Test Bank for Organic Chemistry 2nd Edition by Klein

Chapter Fourteen

Topic: Introduction to Ethers

Section: 14.1

1. Which of the following compounds is(are) classified as ethers?

A) I

B) II & IV

C) III

D) I & III

E) all of these Ans: E

Topic: Nomenclature of Ethers

Section: 14.2

Difficulty Level: Easy

2. What is the common name for CH3CH2CH2OCH2CH2CH3?

A) Dibutylether

B) 1-propoxypropane

C) 1-propoxyhexane

D) dipropyl ether

E) none of these Ans: D


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

D) Diisopropylether

E) none of these

Ans: B


Section: 14.2


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

C) 1,2-diethoxymethane

D) 1,2-diethoxyhexane

E) 1,4-diethoxybutane Ans: E

Topic: Nomenclature

Section: 14.2


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

A) I

B) II

C) III

D) IV

E) none of these

Ans: D

Topic: Nomenclature

Section: 14.2


8. What is the correct structure for dibenzyl ether?

A) I

B) II

C) III

D) IV

E) none of these

Ans: B

Topic: Nomenclature

Section: 14.2


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

Ans: 3-isopropoxy-2-methyloctane

Topic: Nomenclature

Section: 14.2



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

Topic: Nomenclature

Section: 14.2



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

Topic: Nomenclature

Section: 14.2



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


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

B) CH3CH2CH2CH2OH

C) CH3CH2CH2OCH3 D) CH3CH2CH2Cl

E) CH3CH2OCH2CH3

Ans: B


Section: 14.3


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

A) CH3CH2CH2CH2CH3

B) CH3CH2CH2CH2OH

C) CH3CH2CH2OCH3

D) CH3CH2CH2Cl

E) CH3CH2OCH2CHOH

Ans: E


Section: 14.3


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

A) diethyl ether

B) methyl propyl ether

C) 1-butanol

D) 2-butanol

E) pentane Ans: E


Section: 14.3


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

A) II>IV>I>III

B) I>IV>II>III

C) IV>I>II>III

D) III>II>I>IV

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


Section: 14.3


24. Rank the following compounds in decreasing order of water solubility (highest to lowest)

A) II>IV>I>III

B) I>IV>II>III

C) IV>I>II>III

D) III>II>I>IV

E) IV>III>I>II Ans: E


Section: 14.3


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


Topic: Crown ethers

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


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



A) 12-crown-5

B) 12-crown-4

C) 15-crown-5

D) 18-crown-6

E) none of these

Ans: B

Topic: Crown ethers

Section: 14.4



Ans: 18-crown-6

Topic: Crown ethers

Section: 14.4



Ans: 18-crown-6

Topic: Preparation of ethers

Section: 14.5


35. Predict the product for the following reaction.

A) Propene

B) Diethyl ether

C) 1-hexanol

D) 1-propoxypropane Ans: D


Section: 14.5



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?

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?

A) CH3ONa + (CH3)3CBr

B) CH3OH + (CH3)3COH in presence of H2SO4 at 140 C

C) CH3Cl + (CH3)3CBr in presence of NaOH

D) (CH3)3CONa + CH3Br Ans: D


Section: 14.5


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.

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

D) 2-ethoxy-3-methylpentane

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


Section: 14.5



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


Section: 14.5



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


Section: 14.5



Ans:


Section: 14.5


52. . Predict the product for the following reaction. Ans:


Section: 14.5


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

Ans:

OR

OR


Section: 14.5


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



Section: 14.6



A) ethanol + phenol

B) phenol + iodoethane

C) iodobenzene + ethanol

D) iodobenzene + iodoethane



Section: 14.6



A) I

B) II

C) III

D) IV

E) V

Ans: C


Section: 14.6



A) I

B) II

C) III

D) IV

E) V

Ans: B


Section: 14.6


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



Ans:


Section: 14.6


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



Section: 14.7



A) 2-ethyl-3-isopropyl-2-methyloxirane

B) 1-ethyl-2-isopropyl-1-methyloxirane

C) 2,4-dimethyloxyhexane

D) 1-ethyl-2,4-dimethyloxyhexane

E) 3-ethyl-2-isopropyl-3-methyloxirane Ans: A


Section: 14.7


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



Ans: (2S, 3R)-2-ethyl-3-phenyloxirane


Section: 14.7


71. Provide the common name for the following compound.

Ans: 1,4-dioxane


Section: 14.7



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:


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

A) I

B) II

C) III

D) IV

Ans: D


Section: 14.8


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

A) I

B) II

C) III

D) IV

Ans: A


Section: 14.8



A) I

B) II

C) III

D) IV

Ans: C


Section: 14.8



1-methylcyclohexene + mCPBA Ans:


Section: 14.8



Ans: mCPBA


Section: 14.8



A) I

B) II

C) III

D) IV

Ans: D


Section: 14.8



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:


Section: 14.9



Ans:


Section: 14.9



Ans:


Section: 14.9



Ans:


Section: 14.9



Ans:

Topic: Reactions of epoxides

Section: 14.10



A) I

B) II

C) III

D) IV



Section: 14.10



A) I

B) II

C) III

D) IV



Section: 14.10



A) I

B) II

C) III

D) IV



Section: 14.10



A) I

B) II

C) III

D) IV



Section: 14.10



A) I

B) II

C) III

D) IV

E) none of these

Ans: C


Section: 14.10



Ans: HCl


Section: 14.10



Ans: CH3OH/H2SO4


Section: 14.10



A) I

B) II

C) III

D) IV



Section: 14.10



A) I

B) II

C) III

D) IV



Section: 14.10



A) I

B) II

C) III

D) IV



Section: 14.10



Ans:


Section: 14.10



Ans:


Section: 14.10



Ans: 1. mCPBA

2. CH3MgBr

3. H2O


Section: 14.10



Ans: 1. LiAlH4

2. H2O


Section: 14.10



Ans: 1. mCPBA

2. NH3


Section: 14.10



Ans: 1. 2. H2O


Section: 14.10


107. Provide a stepwise curved arrow mechanism for the following reaction.

Ans:

Topic: Nomenclature of Thiols /sulfides

Section: 14.11


108. What is the correct structure for 3-methyl-1-hexanethiol?

Ans:


Section: 14.11


109. What is the correct structure for phenylthiol?

Ans:


Section: 14.11



Ans: 5-methyl-2-heptanethiol


Section: 14.11



Ans: 5-mercapto-2-methyl-1-hexanol


Section: 14.11


112. What is the common name for the following compound?

Ans: Methyl pentyl sulfide


Section: 14.11



Ans: 2-ethylthiohexane

Topic: Preparation of Thiols /sulfides

Section: 14.11



Ans:


Section: 14.11



Ans:


Section: 14.11



Ans:


Section: 14.11



Ans:

Topic: Reactions of Thiols/sulfides

Section: 14.11


118. Predict the major product for the following reaction.

Ans:


Section: 14.11



A) I

B) II

C) III

D) IV



Section: 14.11



Ans:


Section: 14.11



A) I

B) II

C) III

D) IV



Section: 14.11



A) I

B) II

C) III

D) IV

E) II & IV Ans: D

Topic: Synthesis

Section: 14.12


123. Provide a stepwise synthesis for the following.

Ans:

Topic: Synthesis

Section: 14.12



Ans:

Topic: Synthesis

Section: 14.12



Ans:

Topic: Synthesis

Section: 14.12



Ans:

Topic: Synthesis

Section: 14.12



Ans:

Topic: Synthesis

Section: 14.12



Ans:

Topic: Synthesis

Section: 14.12



Ans:

Topic: Synthesis

Section: 14.12



Ans:

Topic: Spectroscopy

Section: 14, 15.6, 16.10, 16.12 Difficulty Level: Medium

131.

A compound with molecular formula C6H14O displays the following IR, 1HNMR and 13CNMR spectra. Propose a structure for this compound. IR: 1200cm-1

SDBS Ans:

Topic: Spectroscopy

Section: 14, 15.6, 16.10, 16.12 Difficulty Level: Medium

132.

A compound with molecular formula C5H12O2 displays the following IR, 1HNMR and 13CNMR spectra. Propose a structure for this compound. IR: 1200cm-1

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