Question 1

Which of the following is not normally considered to be a nucleophile?

Accepted Answer

A)  NH3
B)  NH2CH3
C)   3 
B)  NH2CH3 
C)     
D)  CH3CH2+" class="answers-bank-image d-inline" rel="preload" >
D)  CH3CH2+E) B) and C)
F) All of the above

Question 2

Idenitfy the halide(s)that react in a SN1 reaction.
A)benzyl bromide
B)bromobenzene
C)1-bromo-1-butene
D)1-bromo-2-butene
E)2-bromo-2-phenylpropane

Accepted Answer

Question 3

Which of the following is classified as a vinyl halide?

Accepted Answer

A)  CH3CH 3CH   CHOH 
B)  CH3CH   CHCl 
C)  CH3CH   CHCH2Cl 
D)  CH3CH2CH2CH2Br 
E)  BrCH2CH   CH2" class="answers-bank-image d-inline" rel="preload" > CHOH
B)  CH3CH 3CH   CHOH 
B)  CH3CH   CHCl 
C)  CH3CH   CHCH2Cl 
D)  CH3CH2CH2CH2Br 
E)  BrCH2CH   CH2" class="answers-bank-image d-inline" rel="preload" > CHCl
C)  CH3CH 3CH   CHOH 
B)  CH3CH   CHCl 
C)  CH3CH   CHCH2Cl 
D)  CH3CH2CH2CH2Br 
E)  BrCH2CH   CH2" class="answers-bank-image d-inline" rel="preload" > CHCH2Cl
D)  CH3CH2CH2CH2Br
E)  BrCH2CH 3CH   CHOH 
B)  CH3CH   CHCl 
C)  CH3CH   CHCH2Cl 
D)  CH3CH2CH2CH2Br 
E)  BrCH2CH   CH2" class="answers-bank-image d-inline" rel="preload" > CH2F) B) and C)
G) C) and D)

Question 4

Which of the following is a secondary alkyl halide?

Accepted Answer

A)  CH3Br
B)  (CH3) 3CBr
C)  (CH3) 2CHBr
D)  (CH3) 2CHCH2BrE) A) and B)
F) C) and D)

Question 5

Provide the structure of the major organic product of the following reaction.

Accepted Answer

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

Question 6

Which of the following alkyl halides gives the slowest SN2 reaction?

Accepted Answer

A)  CH3CH2Cl
B)   N2 reaction? 
A)  CH3CH2Cl 
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
C)   N2 reaction? 
A)  CH3CH2Cl 
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
D)   N2 reaction? 
A)  CH3CH2Cl 
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
E)   N2 reaction? 
A)  CH3CH2Cl 
B)     
C)     
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >F) All of the above
G) A) and E)

Question 7

Which of the following alkyl bromides undergoes solvolysis in methanol without rearrangement?

Accepted Answer

A)  (R) -2-bromo-3-ethylpentane
B)  (S) -2-bromo-3-ethylpentane
C)  (R) -3-bromo-2-methylpentane
D)  (S) -3-bromo-2-methylpentane
E)  3-bromo-3-ethylpentaneF) A) and E)
G) B) and E)

Question 8

Provide the structure of the major organic product(s)of the following reaction.

Accepted Answer

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

Question 9

Provide the major organic products(s)of the reaction shown:.

Accepted Answer

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

Question 10

The specific rotation of optically pure (R) -C6H5CHOHCH3 is -42.3°. An optically pure sample of (R) -C6H5CHClCH3 was converted into the corresponding alcohol via an SN2 reaction. What is the specific rotation of the product?

Accepted Answer

A)  -42.3°
B)  between 0° and -42.3°
C)  between +42.3° and 0°
D)  +42.3°E) A) and B)
F) A) and C)

Question 11

Which of the following is not a nucleophile?

Accepted Answer

A)  "CH3NH2"
B)  "PH3"
C)  "+CH3"
D)   3NH2  
B)   PH3  
C)   +CH3  
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >
E)   3NH2  
B)   PH3  
C)   +CH3  
D)     
E)    " class="answers-bank-image d-inline" rel="preload" >F) A) and E)
G) All of the above

Question 12

Why are vinylic halides unreactive in both SN2 and SN1 reactions?

Accepted Answer

Vinylic halides do not undergo S_N2 reacti...

Question 13

Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide?

Accepted Answer

A)  These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom.
B)  Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects.
C)  tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density.
D)  tert-Butoxide is more nucleophilic because it is more basic.
E)  none of the aboveF) D) and E)
G) B) and C)

Question 14

Rank the species below in order of increasing nucleophilicity in protic solvents:
CH3CO2- , CH3S- , HO- , H2O.

Accepted Answer

H₂O < CH₃CO₂^- ...

Question 15

Provide the structure of the major organic product of the following reaction.

Accepted Answer

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

Question 16

Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above SN2 reaction?

Accepted Answer

A)  no change
B)  doubles the rate
C)  triples the rate
D)  quadruples the rate
E)  rate is halvedF) A) and B)
G) A) and C)

Question 17

When nucleophile and leaving group are contained in the same molecule, is intermolecular or intramolecular reaction favored? Explain.

Accepted Answer

The answer depends on the concentration ...

Question 18

A 1,2-methyl shift occurs when which of the following iodides is heated in ethanol?

Accepted Answer

A)  C6H5CHICH(CH3) 2
B)  (CH3) 2CHCHICH3
C)  (CH3) 3CCH2CH2I
D)  (CH3) 2C=CHI
E)  (CH3) 3CCHICH2CH3F) C) and D)
G) A) and E)

Question 19

Which of the following best explains why SN1 reactions involving a neutral reactant are faster in polar solvents?

Accepted Answer

A)  The substrate is more soluble in polar solvents.
B)  The substrate is less soluble in polar solvents.
C)  The nucleophile is solvated by polar solvents.
D)  Solvation by polar solvents stabilizes the carbocation.
E)  Solvation by polar solvents stabilizes the transition state.F) D) and E)
G) B) and C)

Question 20

Which of the following best describes the carbon-chlorine bond of an alkyl chloride?

Accepted Answer

A)  nonpolar; no dipole
B)  polar; δ+ at carbon and δ- at chlorine
C)  polar; δ- at carbon and δ+ at chlorine
D)  ionic
E)  none of the aboveF) B) and D)
G) A) and D)

Exam 9: Substitution Reactions of Alkyl Halides

Which of the following alkyl bromides undergoes solvolysis in methanol without rearrangement?

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Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide?

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A 1,2-methyl shift occurs when which of the following iodides is heated in ethanol?

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When nucleophile and leaving group are contained in the same molecule, is intermolecular or intramolecular reaction favored? Explain.

Correct AnswerverifiedThe answer depends on the concentration ...View AnswerShow Answer

Idenitfy the halide(s)that react in a SN1 reaction. A)benzyl bromide B)bromobenzene C)1-bromo-1-butene D)1-bromo-2-butene E)2-bromo-2-phenylpropane

Correct AnswerverifiedShow Answer

Rank the species below in order of increasing nucleophilicity in protic solvents: CH3CO2- , CH3S- , HO- , H2O.

Correct AnswerverifiedH2O < CH3CO2- ...View AnswerShow Answer

Which of the following is classified as a vinyl halide?

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Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above SN2 reaction?

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Which of the following is not a nucleophile?

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Provide the structure of the major organic product of the following reaction.

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The specific rotation of optically pure (R) -C6H5CHOHCH3 is -42.3°. An optically pure sample of (R) -C6H5CHClCH3 was converted into the corresponding alcohol via an SN2 reaction. What is the specific rotation of the product?

Correct AnswerverifiedShow Answer

Which of the following best explains why SN1 reactions involving a neutral reactant are faster in polar solvents?

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Provide the structure of the major organic product of the following reaction.

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Which of the following alkyl halides gives the slowest SN2 reaction?

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Which of the following is a secondary alkyl halide?

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Why are vinylic halides unreactive in both SN2 and SN1 reactions?

Correct AnswerverifiedVinylic halides do not undergo SN2 reacti...View AnswerShow Answer

Provide the structure of the major organic product(s)of the following reaction.

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Provide the major organic products(s)of the reaction shown:.

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Which of the following is not normally considered to be a nucleophile?

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Which of the following best describes the carbon-chlorine bond of an alkyl chloride?

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The answer depends on the concentration ...
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Idenitfy the halide(s)that react in a S_N1 reaction. A)benzyl bromide B)bromobenzene C)1-bromo-1-butene D)1-bromo-2-butene E)2-bromo-2-phenylpropane

Correct Answer
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Rank the species below in order of increasing nucleophilicity in protic solvents: CH₃CO₂^- , CH₃S^- , HO^- , H₂O.

Correct Answer
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H₂O < CH₃CO₂^- ...
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Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above S_N2 reaction?

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The specific rotation of optically pure (R) -C₆H₅CHOHCH₃ is -42.3°. An optically pure sample of (R) -C₆H₅CHClCH₃ was converted into the corresponding alcohol via an S_N2 reaction. What is the specific rotation of the product?

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Which of the following best explains why S_N1 reactions involving a neutral reactant are faster in polar solvents?

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Which of the following alkyl halides gives the slowest S_N2 reaction?

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Why are vinylic halides unreactive in both S_N2 and S_N1 reactions?

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Vinylic halides do not undergo S_N2 reacti...
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