Question 1

Give the mechanism including the transition state.

Accepted Answer

The answer of Give the mechanism including the transition state....

Question 2

Provide a detailed, stepwise mechanism for the reaction below.
(CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CN + I-

Accepted Answer

Question 3

Which of the following alkyl bromides is likely to undergo rearrangement by a 1, 2-methyl shift?

Accepted Answer

A)  benzyl bromide
B)  2-bromo-3-ethylpentane
C)  3-bromo-3-methylpentane
D)  2-bromo-3, 3-dimethylpentane
E)  3-bromo-2, 3-dimethylpentaneF) A) and C)
G) None of the above

Question 4

Give the mechanism including the transition state.

Accepted Answer

The answer of Give the mechanism including the transition state....

Question 5

Give the name(s) of the product(s) of the SN1 reaction of 3-bromo-2,2-dimethylbutane with water.

Accepted Answer

A)  2,2-dimethyl-1-butanol
B)  3,3-dimethyl-2-butanol
C)  3,3-dimethyl-1-butanol
D)  2,3-dimethyl-2-butanol
E)  2,3-dimethyl-1-butanolF) B) and C)
G) None of the above

Question 6

The hydrolysis of tert-butyl chloride proceeds more rapidly in a solvent mixture which is 70% water/30% acetone than in one which is 30% water/70% acetone. Why?

Accepted Answer

A)  The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture.
B)  The reaction proceeds by an SN2 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water.
C)  The reaction proceeds by an SN1 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water.
D)  The solvent which contains a greater percentage of water is less polar, and this destabilizes the tert-butyl chloride.
E)  none of the aboveF) A) and B)
G) A) and C)

Question 7

Which of the following solvents is aprotic?

Accepted Answer

A)  CH3CH2OH
B)  CH3CH2CH2NH2
C)  CH3CH2OCH2CH3
D)  CH3CH2NHCH3
E)   3CH2OH 
B)  CH3CH2CH2NH2 
C)  CH3CH2OCH2CH3 
D)  CH3CH2NHCH3 
E)    " class="answers-bank-image d-inline" rel="preload" >F) All of the above
G) A) and B)

Question 8

Which of the following statements is generally true for SN1 reactions?

Accepted Answer

A)  Complete inversion of configuration occurs.
B)  These reactions are favored by nonpolar solvents.
C)  These reactions are favored by polar solvents.
D)  Reaction rates depend only on the concentration of the nucleophile.
E)  The mechanism is a one-step back attack.F) A) and B)
G) All of the above

Question 9

A student attempted to prepare 1-chlorobutane by treating 1-butanol with NaCl in acetone. Was the student successful? Explain.

Accepted Answer

The student was unsuccessful. The reacti...

Question 10

Provide the major organic product(s)in the reaction below.

Accepted Answer

The answer of Provide the major organic product(s)in the reaction...

Question 11

Which of the following species is the least nucleophilic?

Accepted Answer

A)  (CH3) 3CO-
B)  H2O
C)  (CH3) 3N
D)  BF3
E)  CN-F) A) and D)
G) All of the above

Question 12

Which of the following is the rate law for SN1 mechanisms?

Accepted Answer

A)  Rate = k[Alkyl Halide] [Nucleophile]
B)  Rate = k[Nucleophile]
C)  Rate = k[Alkyl Halide]
D)  Rate = k[Alkyl Halide] [Nucleophile] + k2[Alkyl Halide]
E)  Rate = k1[Alkyl Halide] + k2[Nucleophile]F) A) and B)
G) A) and C)

Question 13

Which of the following factors has no effect on the rate of SN1 reactions?

Accepted Answer

A)  the nature of the alkyl halide
B)  the nature of the leaving group
C)  the concentration of the alkyl halide
D)  the concentration of the nucleophile
E)  the value of the rate constantF) B) and E)
G) B) and C)

Question 14

Which of the following does not provide evidence that there are two different mechanisms for nucleophilic substitution?

Accepted Answer

A)  reaction products when CH3I is used as the substrate
B)  reaction products when (CH3) 3CCH2I is used as substrate
C)  the stereochemistry of nucleophilic substitutions
D)  the effect of nucleophile concentration on rateE) C) and D)
F) A) and B)

Question 15

Rank the species below in order of leaving group capabilities in SN2 reactions (worst leaving group to best):
CH3O-, H2O, C6H5SO3-, H2N-.

Accepted Answer

H₂N^- < CH₃O^- <...

Question 16

Provide the major organic product(s)in the reaction below.

Accepted Answer

The answer of Provide the major organic product(s)in the reaction...

Question 17

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

Accepted Answer

CH₃Br < CH₃C...

Question 18

Identify the mechanism. .

Accepted Answer

A)  SN1
B)  SN2
C)  E1
D)  E2
E)  none of the aboveF) None of the above
G) B) and C)

Question 19

Identify the strongest nucleophile in an SN2 reaction.

Accepted Answer

A)  isopropoxide ion
B)  tert-butoxide ion
C)  ethoxide ion
D)  tert-pentoxide ionE) A) and B)
F) A) and C)

Question 20

Which of the following correctly describes SAM, a biological methylating agent?

Accepted Answer

A)  It contains a Cl bonded to a 1° carbon.
B)  It contains a methyl group bonded to a positively charged sulfur atom.
C)  It contains a methyl ether.
D)  it contains a methyl group bonded to an aromatic ring.
E)  It contains a Br bonded to a phosphorus atom.F) B) and C)
G) All of the above

Exam 9: Substitution Reactions of Alkyl Halides

Identify the strongest nucleophile in an SN2 reaction.

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Which of the following correctly describes SAM, a biological methylating agent?

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Rank the species below in order of leaving group capabilities in SN2 reactions (worst leaving group to best): CH3O-, H2O, C6H5SO3-, H2N-.

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Which of the following does not provide evidence that there are two different mechanisms for nucleophilic substitution?

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Which of the following species is the least nucleophilic?

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Give the name(s) of the product(s) of the SN1 reaction of 3-bromo-2,2-dimethylbutane with water.

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Which of the following solvents is aprotic?

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Which of the following factors has no effect on the rate of SN1 reactions?

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Which of the following alkyl bromides is likely to undergo rearrangement by a 1, 2-methyl shift?

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Provide a detailed, stepwise mechanism for the reaction below. (CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CN + I-

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The hydrolysis of tert-butyl chloride proceeds more rapidly in a solvent mixture which is 70% water/30% acetone than in one which is 30% water/70% acetone. Why?

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Which of the following is the rate law for SN1 mechanisms?

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Give the mechanism including the transition state.

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Give the mechanism including the transition state.

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Provide the major organic product(s)in the reaction below.

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A student attempted to prepare 1-chlorobutane by treating 1-butanol with NaCl in acetone. Was the student successful? Explain.

Correct AnswerverifiedThe student was unsuccessful. The reacti...View AnswerShow Answer

Identify the mechanism. .

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Provide the major organic product(s)in the reaction below.

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Which of the following statements is generally true for SN1 reactions?

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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

Identify the strongest nucleophile in an S_N2 reaction.

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Rank the species below in order of leaving group capabilities in S_N2 reactions (worst leaving group to best): CH₃O^-, H₂O, C₆H₅SO₃^-, H₂N^-.

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H₂N^- < CH₃O^- <...
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Give the name(s) of the product(s) of the S_N1 reaction of 3-bromo-2,2-dimethylbutane with water.

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Which of the following factors has no effect on the rate of S_N1 reactions?

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Provide a detailed, stepwise mechanism for the reaction below. (CH₃)₂CHCH₂CH₂CH₂I + CN^- → (CH₃)₂CHCH₂CH₂CH₂CN + I^-

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Which of the following is the rate law for S_N1 mechanisms?

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The student was unsuccessful. The reacti...
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Which of the following statements is generally true for S_N1 reactions?

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

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CH₃Br < CH₃C...
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