Question 1

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) None of the above

Question 2

What is the starting material in the reaction shown below?

Accepted Answer

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

Question 3

Which of the following structures have the correct common name?

Accepted Answer

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

Question 4

Identify the nucleophile and type of substitution reaction in the following: -,Sn1 B) CN-,Sn2 C) Br-,Sn1 D) Br-,Sn2" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  CN-,Sn1
B)  CN-,Sn2
C)  Br-,Sn1
D)  Br-,Sn2E) B) and C)
F) A) and B)

Question 5

What is the IUPAC name of the following compound?

Accepted Answer

A)  (R) -3-Bromo-1-methylcyclohexene
B)  (S) -3-Bromo-1-methylcyclohexene
C)  (S) -1-Bromo-3-methyl-2-cyclohexene
D)  (R) -1-Bromo-3-methyl-2-cyclohexeneE) A) and C)
F) B) and C)

Question 6

Which of the following anions is the most nucleophilic in polar aprotic solvents?

Accepted Answer

A)  F-
B)  Cl-
C)  Br-
D)  I-E) C) and D)
F) None of the above

Question 7

What is the IUPAC name of the following compound?

Accepted Answer

A)  (3R,4R) -3-chloro-4-methylhexane
B)  (3R,4S) -3-chloro-4-methylhexane
C)  (3S,4R) -3-chloro-4-methylhexane
D)  (3S,4S) -3-chloro-4-methylhexaneE) A) and D)
F) A) and C)

Question 8

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

Question 9

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

Accepted Answer

A)  I 
B)  IV 
C)  I 
D)  IV < III < I < IIE) All of the above
F) B) and D)

Question 10

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) A) and B)

Question 11

Which alkyl halide will form the most stable carbocation?

Accepted Answer

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

Question 12

What is the starting material in the reaction shown below?

Accepted Answer

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

Question 13

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 C)
F) None of the above

Question 14

Rank the following compounds in order of increasing SN1 reactivity? N1 reactivity?   A) I > II > III > IV B) IV > I > II > III C) IV > III > II > I D) III > II > I > IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 15

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) B) and C)

Question 16

Rank the following molecules in order of increasing polarity,putting the least polar first.

Accepted Answer

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

Question 17

Rank the alkyl halides in order of decreasing SN2 reactivity,putting the most reactive first. N2 reactivity,putting the most reactive first.   A) I > II > III B) II > I > III C) III > I > II D) I > III > II" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  I > II > III
B)  II > I > III
C)  III > I > II
D)  I > III > IIE) A) and C)
F) C) and D) B

Question 18

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

Accepted Answer

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

Question 19

Which of the following alkyl halides will react fastest with CH3OH in an SN1 mechanism? 3OH in an SN1 mechanism?   A) I B) II C) III D) IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 20

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 C)
F) C) and D) A

Exam 7: Alkyl Halides and Nucleophilic Substitution

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

Correct AnswerverifiedShow Answer

What is the starting material in the reaction shown below?

Correct AnswerverifiedShow Answer

Which of the following structures have the correct common name?

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Identify the nucleophile and type of substitution reaction in the following:

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What is the IUPAC name of the following compound?

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Which of the following anions is the most nucleophilic in polar aprotic solvents?

Correct AnswerverifiedShow Answer

What is the IUPAC name of the following compound?

Correct AnswerverifiedShow Answer

Which of the following statements about the Hammond postulate is not 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

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

Correct AnswerverifiedShow Answer

Which alkyl halide will form the most stable carbocation?

Correct AnswerverifiedA

What is the starting material in the reaction shown below?

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

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Rank the following compounds in order of increasing SN1 reactivity?

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

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Rank the following molecules in order of increasing polarity,putting the least polar first.

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Rank the alkyl halides in order of decreasing SN2 reactivity,putting the most reactive first.

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Rank the following in order of decreasing nucleophilicity,putting the most nucleophilic first.

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Which of the following alkyl halides will react fastest with CH3OH in an SN1 mechanism?

Correct AnswerverifiedShow Answer

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

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A

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Rank the following compounds in order of increasing S_N1 reactivity?

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

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Rank the alkyl halides in order of decreasing S_N2 reactivity,putting the most reactive first.

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B

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Which of the following alkyl halides will react fastest with CH₃OH in an S_N1 mechanism?

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A