Question 1

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) A) and B)
F) C) and D)

Question 2

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 D)
F) B) and C)

Question 3

Which of the following is a polar aprotic solvent?

Accepted Answer

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

Question 4

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) A) and C)
F) All of the above

Question 5

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) A) and B)
F) C) and D)

Question 6

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) None of the above
F) A) and B)

Question 7

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) None of the above

Question 8

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) All of the above
F) None of the above

Question 9

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) B) and D)
F) None of the above

Question 10

Which of the following is the most nucleophilic?

Accepted Answer

A)  CH4
B)  H2O
C)  NH3
D)  HFE) A) and B)
F) All of the above

Question 11

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 D)
F) B) and C)

Question 12

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) All of the above

Question 13

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) B) and C)
F) A) and C)

Question 14

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) None of the above
F) All of the above

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) All of the above

Question 16

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

Accepted Answer

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

Question 17

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 B)
F) A) and C)

Question 18

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) B) and D)
F) B) and C)

Question 19

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) B) and D)
F) B) and C)

Question 20

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) B) and C)
F) A) and B)

Exam 7: Alkyl Halides and Nucleophilic Substitution

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

Correct AnswerverifiedShow Answer

Which of the following is a polar aprotic solvent?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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.

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What is the IUPAC name of the following compound?

Correct AnswerverifiedShow Answer

What is the IUPAC name of the following compound?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following is the most nucleophilic?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following structures have the correct common name?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct Answer
verified

Correct Answer
verified

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

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

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

Correct Answer
verified

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

Correct Answer
verified

Correct Answer
verified