Question 1

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IV

Question 2

The reaction of 1-bromobutane with sodium hydroxide affords the substitution product 1-butanol.What would happen to the rate of the reaction if the concentration of both 1-bromobutane and sodium hydroxide were doubled?

Accepted Answer

A)  The rate remains the same.
B)  The rate decreases by a factor of 2.
C)  The rate increases by a factor of 2.
D)  The rate increases by a factor of 4.

Question 3

Which of the following is not a characteristic of an SN1 reaction?

Accepted Answer

A)  The rate is proportional to the concentration of substrate.
B)  The reaction is favored in polar protic solvents.
C)  The rate is independent of the concentration of the nucleophile.
D)  The electrophilic carbon undergoes inversion of stereochemistry.

Question 4

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 > I

Question 5

Which of the following rate laws describes the kinetics of an SN1 reaction?

Accepted Answer

A)  Rate = k[alkyl halide]
B)  Rate = k[alkyl halide][nucleophile]
C)  Rate = k[nucleophile]
D)  Rate = k[solvent]

Question 6

The reaction of bromoethane with sodium acetate affords the substitution product methyl acetate.What is the effect of doubling the concentration of sodium acetate on the rate of the reaction?

Accepted Answer

A)  The rate remains the same.
B)  The rate decreases by a factor of 2.
C)  The rate increases by a factor of 2.
D)  The rate increases by a factor of 4.

Question 7

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.

Question 8

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

Accepted Answer

A)  F-
B)  Cl-
C)  Br-
D)  I-

Question 9

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) 2CHBr

Question 10

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 IV

Question 11

Which of the following is the most nucleophilic?

Accepted Answer

A)  CH4
B)  H2O
C)  NH3
D)  HF

Question 12

What is the IUPAC name of the following compound?

Accepted Answer

A)  2-Methyl-4-chloropentane
B)  2-Chloro-4-methylpentane
C)  2-Chloro-1-isopropylpropane
D)  2-Chloro-2-methylpentane

Question 13

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.

Question 14

Which of the following statements about the reactions of alkyl halides is true?

Accepted Answer

A)  The characteristic reactions of alkyl halides are addition and elimination.
B)  The characteristic reactions of alkyl halides are addition and substitution.
C)  The characteristic reactions of alkyl halides are elimination and substitution.
D)  The characteristic reactions of alkyl halides are oxidation and reduction.

Question 15

What is the starting material in the reaction shown below?

Accepted Answer

A)  I
B)  II
C)  III
D)  IV

Question 16

The reaction of tert-butyl bromide,(CH3) 3CBr,with ethanol affords the substitution product tert-butyl ethyl ether,(CH3) 3COCH2CH3,in acidic conditions.What would happen to the rate of the reaction if the concentration of ethanol was doubled?

Accepted Answer

A)  The rate remains the same.
B)  The rate decreases by a factor of 2.
C)  The rate increases by a factor of 2.
D)  The rate increases by a factor of 4.

Question 17

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

Accepted Answer

A)  Only I
B)  Only II
C)  I and II
D)  None

Question 18

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.

Question 19

Which of the following statements about carbocation stability is true?

Accepted Answer

A)  Carbocations are stabilized by electron-withdrawing inductive effects only.
B)  Carbocations are stabilized by electron-withdrawing inductive effects and hyperconjugation.
C)  Carbocations are stabilized by electron-donating inductive effects only.
D)  Carbocations are stabilized by electro-donating inductive effects and hyperconjugation.

Question 20

Which of the following statements is true?

Accepted Answer

A)  All good leaving groups are strong bases with weak conjugate acids.
B)  Left-to-right across a row of the periodic table,leaving group ability decreases.
C)  Down a column of the periodic table,leaving group ability decreases.
D)  The conjugate bases of strong acids are good leaving groups.

Exam 7: Alkyl Halides and Nucleophilic Substitution

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

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The reaction of bromoethane with sodium acetate affords the substitution product methyl acetate.What is the effect of doubling the concentration of sodium acetate on the rate of the reaction?

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Which of the following statements is true?

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

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The reaction of 1-bromobutane with sodium hydroxide affords the substitution product 1-butanol.What would happen to the rate of the reaction if the concentration of both 1-bromobutane and sodium hydroxide were doubled?

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Which of the following structures have the correct common name?

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Which of the following is not a characteristic of an SN1 reaction?

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

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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 SN1 reaction mechanism is true?

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

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Which of the following statements about carbocation stability is true?

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Which of the following rate laws describes the kinetics of an SN1 reaction?

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What is the starting material in the reaction shown below?

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What is the IUPAC name of the following compound?

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Which of the following is the most nucleophilic?

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Which of the following statements about the reactions of alkyl halides is true?

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

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

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The reaction of tert-butyl bromide,(CH3) 3CBr,with ethanol affords the substitution product tert-butyl ethyl ether,(CH3) 3COCH2CH3,in acidic conditions.What would happen to the rate of the reaction if the concentration of ethanol was doubled?

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

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Which of the following is not a characteristic of an S_N1 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 rate laws describes the kinetics of an S_N1 reaction?

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The reaction of tert-butyl bromide,(CH₃) ₃CBr,with ethanol affords the substitution product tert-butyl ethyl ether,(CH₃) ₃COCH₂CH₃,in acidic conditions.What would happen to the rate of the reaction if the concentration of ethanol was doubled?

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