Question 1

Which of the following is a geminal dihalide?

Accepted Answer

A)   cis-1,2-dibromocyclopentane
B)   3,3-dichloropentane
C)   trans-1,4-diiodocyclohexane
D)   isobutyl chloride
E)   1,3-dibromoheptane

Question 2

List the following bromides in order of their increasing reactivity as substrates in SN1 reactions: PhBr, PhCH2Br, and PhCH(CH3)Br.

Accepted Answer

PhBr < PhC...

Question 3

Which of the following is a secondary alkyl halide?

Accepted Answer

A)   methyl bromide
B)   isopropyl chloride
C)   t-butyl iodide
D)   propyl bromide
E)   isobutyl chloride

Question 4

Provide the structure of the major organic product which results in the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 5

Which of the following is a secondary halide?

Accepted Answer

A)   ClCH2CH2C(CH3) 3
B)   ClCH2CH2CH(CH3) 2
C)   (CH3) 2CClCH2CH3
D)   (CH3) 3CCHClCH3
E)   ClCH2C(CH3) CH2CH3

Question 6

Provide the structure of the major organic product in the following reaction.
(CH3)3N + CH3CH2CH2I →

Accepted Answer

Question 7

List the following compounds in order of increasing reactivity in an SN1 reaction.
CH3Br, CH3CH2CH2I, (CH3)3CI, CH3CHBrCH3, CH3CHICH3

Accepted Answer

CH₃Br < CH₃C...

Question 8

Arrange the following alkyl halides in order of increasing boiling point:
CH3CH2Br, CH3CH2CH2Br, (CH3)2CHBr, CH3CH2F.

Accepted Answer

CH₃CH₂F < CH...

Question 9

Arrange the following species in order of increasing nucleophilicity:
CH3CH2S-, CH3CH2O-, (CH3)3CO-, (CH3)3COH.

Accepted Answer

(CH₃)₃COH < ...

Question 10

Provide the structure of the major organic product in the reaction below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 11

What general classification is given to the molecule below?

Accepted Answer

A)   primary chloride
B)   secondary chloride
C)   tertiary chloride
D)   vinyl chloride
E)   benzyl chloride

Question 12

Provide the structure of the major alkene product of the reaction below.

Accepted Answer

The answer of Provide the structure of the major alkene...

Question 13

Provide the structure of the major organic product which results when (S)-2-iodopentane is treated with KCN in DMF.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 14

Which of the following best describes DDT?

Accepted Answer

A)   a chlorocarbon used to decaffeinate coffee beans
B)   a polybrominated organic compound used as a herbicide
C)   a Freon used as a foaming agent
D)   a mixed alkyl halide used as an anesthetic
E)   a polychlorinated organic compound used as an insecticide

Question 15

Provide the structure of the major organic products which result in the reaction below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 16

Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 17

Provide an acceptable name for CHCl3.

Accepted Answer

chloroform...

Question 18

Provide a detailed, stepwise mechanism for the reaction below.
(CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CH2CN + I-

Accepted Answer

Question 19

Which of the following alkyl halides can produce only a single alkene product from when treated with sodium methoxide?

Accepted Answer

A)   2-chloro-2-methylpentane
B)   3-chloro-3-ethylpentane
C)   3-chloro-2-methylpentane
D)   2-chloro-4-methylpentane
E)   2-chloro-3-ethylpentane

Question 20

The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?

Accepted Answer

A)   SN1
B)   SN2
C)   E1
D)   E2
E)   Ecb

Exam 6: Alkyl Halides; Nucleophilic Substitution

Which of the following is a secondary halide?

Correct AnswerverifiedShow Answer

Which of the following alkyl halides can produce only a single alkene product from when treated with sodium methoxide?

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Arrange the following alkyl halides in order of increasing boiling point: CH3CH2Br, CH3CH2CH2Br, (CH3)2CHBr, CH3CH2F.

Correct AnswerverifiedCH3CH2F < CH...View AnswerShow Answer

Provide the structure of the major organic product in the following reaction. (CH3)3N + CH3CH2CH2I →

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The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?

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Provide the structure of the major organic products which result in the reaction below.

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Provide an acceptable name for CHCl3.

Correct Answerverifiedchloroform...View AnswerShow Answer

Which of the following is a secondary alkyl halide?

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Provide the structure of the major alkene product of the reaction below.

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Provide the structure of the major organic product which results in the following reaction.

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Provide a detailed, stepwise mechanism for the reaction below. (CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CH2CN + I-

Correct AnswerverifiedShow Answer

Provide the structure of the major organic product which results when (S)-2-iodopentane is treated with KCN in DMF.

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Provide the structure of the major organic product which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.

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Arrange the following species in order of increasing nucleophilicity: CH3CH2S-, CH3CH2O-, (CH3)3CO-, (CH3)3COH.

Correct Answerverified(CH3)3COH < ...View AnswerShow Answer

Which of the following best describes DDT?

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What general classification is given to the molecule below?

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Provide the structure of the major organic product in the reaction below.

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List the following compounds in order of increasing reactivity in an SN1 reaction. CH3Br, CH3CH2CH2I, (CH3)3CI, CH3CHBrCH3, CH3CHICH3

Correct AnswerverifiedCH3Br < CH3C...View AnswerShow Answer

List the following bromides in order of their increasing reactivity as substrates in SN1 reactions: PhBr, PhCH2Br, and PhCH(CH3)Br.

Correct AnswerverifiedPhBr < PhC...View AnswerShow Answer

Which of the following is a geminal dihalide?

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Arrange the following alkyl halides in order of increasing boiling point: CH₃CH₂Br, CH₃CH₂CH₂Br, (CH₃)₂CHBr, CH₃CH₂F.

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CH₃CH₂F < CH...
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Provide the structure of the major organic product in the following reaction. (CH₃)₃N + CH₃CH₂CH₂I →

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Provide an acceptable name for CHCl₃.

Correct Answer
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chloroform...
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Provide a detailed, stepwise mechanism for the reaction below. (CH₃)₂CHCH₂CH₂CH₂I + CN^- → (CH₃)₂CHCH₂CH₂CH₂CH₂CN + I^-

Correct Answer
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Arrange the following species in order of increasing nucleophilicity: CH₃CH₂S^-, CH₃CH₂O^-, (CH₃)₃CO^-, (CH₃)₃COH.

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(CH₃)₃COH < ...
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List the following compounds in order of increasing reactivity in an S_N1 reaction. CH₃Br, CH₃CH₂CH₂I, (CH₃)₃CI, CH₃CHBrCH₃, CH₃CHICH₃

Correct Answer
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CH₃Br < CH₃C...
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List the following bromides in order of their increasing reactivity as substrates in S_N1 reactions: PhBr, PhCH₂Br, and PhCH(CH₃)Br.

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PhBr < PhC...
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