Question 1

Which compound is most likely to follow second-order kinetics in a substitution reaction?

Accepted Answer

A)  CH3Br
B)  (CH3) 3CCH2Br
C)  CH3CH2Br
D)  (CH3) 2CHBrE) C) and D)
F) All of the above

Question 2

Which of the following alkyl halides would react the fastest with -OH in SN2 reaction? CH3CH2Br, CH3CH2Cl, CH3CH2F, CH3CH2I

Accepted Answer

A)  CH3CH2Br
B)  CH3CH2Cl
C)  CH3CH2F
D)  CH3CH2IE) B) and C)
F) C) and D)

Question 3

What is the IUPAC name of the following compound?

Accepted Answer

A)  trans-4-Methylcyclohexyl chloride
B)  trans-p-Chloromethylcyclohexane
C)  trans-4-Methyl-1-chlorocyclohexane
D)  trans-1-Chloro-4-methylcyclohexaneE) All of the above
F) B) and C)

Question 4

Which of the following statements about the Hammond postulate is true?

Accepted Answer

A)  In an exothermic reaction, lowering the energy of the transition state increases the activation energy, Ea.
B)  In an endothermic reaction, the more stable product forms faster.
C)  In an endothermic reaction, the less stable product forms faster.
D)  In an endothermic reaction, the activation energy, Ea, is similar for both products.E) A) and D)
F) A) and C)

Question 5

What is the product of the nucleophilic substitution reaction shown below?

Accepted Answer

A)  Only I
B)  Only II
C)  I and II
D)  NoneE) None of the above
F) B) and C)

Question 6

Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions is true?

Accepted Answer

A)  Involves one step and occurs with retention of configuration.
B)  Involves two steps and occurs with inversion of configuration.
C)  Involves one step and occurs with inversion of configuration.
D)  Involves one step and occurs with racemization.E) A) and B)
F) A) and C)

Question 7

Rank the following in order of decreasing leaving group ability, putting the best first.  II > IV > I B) III > II > I > IV C) IV > I > II > III D) II > III > I > IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  III > II > IV > I
B)  III > II > I > IV
C)  IV > I > II > III
D)  II > III > I > IVE) B) and C)
F) C) and D)

Question 8

Rank the following ions in order of increasing nucleophilicity in polar protic solvents, starting with the least nucleophilic ion.  Rank the following ions in order of increasing nucleophilicity in polar protic solvents, starting with the least nucleophilic ion.   A) I

Accepted Answer

A)  I 
B)  IV 
C)  I 
D)  IV < III < I < IIE) A) and C)
F) C) and D)

Question 9

What is the IUPAC name of the following compound?

Accepted Answer

A)  (
E)  -2-Bromo-3,4-dimethyl-2-pentene
B)  (Z) -1-Bromo-1,2,3-trimethyl-1-butene
C)  (Z) -2-Bromo-3,4-dimethyl-2-pentene
D)  (
E)  -1-Bromo-1,2,3-trimethyl-1-buteneE) B) and C)
F) B) and D)

Question 10

For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs.Then determine which solvent affords the faster reaction.  For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs.Then determine which solvent affords the faster reaction.   A) SN1, H2O B) SN1, DMF C) SN2, H2O D) SN2, DMF" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  SN1, H2O
B)  SN1, DMF
C)  SN2, H2O
D)  SN2, DMFE) None of the above
F) A) and B)

Question 11

What is the product of the nucleophilic substitution reaction shown below?

Accepted Answer

A)  Only I
B)  Only II
C)  I and II
D)  NoneE) None of the above
F) B) and D)

Question 12

Which of the following is the most nucleophilic?

Accepted Answer

A)  CH4
B)  H2O
C)  NH3
D)  HFE) A) and B)
F) A) and C)

Question 13

Which of the following solvents is not a polar protic solvent?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) A) and C)

Question 14

Which of the following statements about the Hammond postulate is not true?

Accepted Answer

A)  The Hammond postulate provides a quantitative estimate of the energy of a transition state.
B)  In endothermic reactions, the transition state is closer in energy to the products.
C)  In exothermic reactions, the transition state is closer in energy to the reactants.
D)  The Hammond postulate provides a qualitative estimate of the energy of a transition state.E) None of the above
F) B) and D)

Question 15

What is the product of the nucleophilic substitution reaction shown below?

Accepted Answer

A)  Only I
B)  Only II
C)  I and II
D)  NoneE) B) and D)
F) A) and B)

Question 16

Which of the following structures have the correct common name?

Accepted Answer

A)  I and II
B)  II and III
C)  II and IV
D)  III and IVE) A) and D)
F) A) and C)

Question 17

Which of the following is a polar aprotic solvent?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) All of the above

Question 18

Pick the solvent that gives the fastest SN2 reaction between CH2CH2Br and -OCH3.

Accepted Answer

A)  CH2CH2OH
B)  CH3OH
C)  DMSO
D)  H2OE) A) and B)
F) A) and C)

Question 19

Rank the following carbocations in order of decreasing stability, putting the most stable first.  II > III B) II > I > III C) III > I > II D) III > II > I" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  I > II > III
B)  II > I > III
C)  III > I > II
D)  III > II > IE) C) and D)
F) None of the above

Question 20

Which of the following statements about an SN1 reaction mechanism is true?

Accepted Answer

A)  The reaction is fastest with primary alkyl halide.
B)  The reaction exhibits a one-step mechanism.
C)  The reaction rate increases as the leaving group ability increases.
D)  The reaction rate increases as the strength of the nucleophile increases.E) A) and B)
F) None of the above

Exam 7: Alkyl Halides and Nucleophilic Substitution

Which of the following statements about the Hammond postulate is true?

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For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs.Then determine which solvent affords the faster reaction.

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Which of the following solvents is not a polar protic solvent?

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Rank the following ions in order of increasing nucleophilicity in polar protic solvents, starting with the least nucleophilic ion.

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What is the product of the nucleophilic substitution reaction shown below?

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Which of the following is a polar aprotic solvent?

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Which of the following is the most nucleophilic?

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What is the product of the nucleophilic substitution reaction shown below?

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What is the IUPAC name of the following compound?

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Which of the following structures have the correct common name?

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Which of the following statements about the Hammond postulate is not true?

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What is the IUPAC name of the following compound?

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Rank the following in order of decreasing leaving group ability, putting the best first.

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Which of the following statements about an SN1 reaction mechanism is true?

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Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions is true?

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Rank the following carbocations in order of decreasing stability, putting the most stable first.

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Pick the solvent that gives the fastest SN2 reaction between CH2CH2Br and -OCH3.

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What is the product of the nucleophilic substitution reaction shown below?

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Which of the following alkyl halides would react the fastest with -OH in SN2 reaction? CH3CH2Br, CH3CH2Cl, CH3CH2F, CH3CH2I

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Which compound is most likely to follow second-order kinetics in a substitution reaction?

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Which of the following statements about an S_N1 reaction mechanism is true?

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Which of the following statements about the S_N2 mechanism for nucleophilic substitution reactions is true?

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Pick the solvent that gives the fastest S_N2 reaction between CH₂CH₂Br and ^-OCH₃.

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Which of the following alkyl halides would react the fastest with ^-OH in S_N2 reaction? CH₃CH₂Br, CH₃CH₂Cl, CH₃CH₂F, CH₃CH₂I

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