Question 1

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

Question 2

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

Question 3

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.E) A) and B)
F) B) and C)

Question 4

Which of the following statements about SN2 reactions is true?

Accepted Answer

A)  The rate of reaction is dependent on just the substrate.
B)  The fastest reaction will occur with a tertiary alkyl halide.
C)  The mechanism is a two-step process.
D)  Displacement occurs with inversion of configuration.E) None of the above
F) A) and D)

Question 5

What is the IUPAC name of the following compound?

Accepted Answer

A)  2-Bromo-5-methyloctane
B)  2-Bromo-3-methylheptane
C)  2-Bromo-5-methylheptane
D)  6-Bromo-3-methylheptaneE) None of the above
F) All of the above

Question 6

The reaction of what nucleophile and substrate is represented by the following transition state?

Accepted Answer

A)  Methanol with 2-bromopropane
B)  Methoxide with 2-bromopropane
C)  Methoxide with 1-bromopropane
D)  Methanol with 1-bromopropaneE) B) and D)
F) C) and D)

Question 7

What is the IUPAC name of the following compound?

Accepted Answer

A)  (R) -3-Chloro-6-ethyloctane
B)  (S) -3-Chloro-6-ethyloctane
C)  (S) -6-Chloro-3-ethyloctane
D)  (R) -6-Chloro-3-ethyloctaneE) A) and D)
F) B) and D)

Question 8

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]E) None of the above
F) A) and D) A

Question 9

What is the starting material in the reaction shown below?

Accepted Answer

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

Question 10

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

Question 11

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.E) C) and D)
F) A) and B)

Question 12

What is the IUPAC name of the following compound?

Accepted Answer

A)  2-Chloro-4-isopropyl-2,6-dimethyloctane
B)  2-Chloro-4-isopropyl-2,7-dimethylnonane
C)  2,6-Dimethyl-2-chloro-4-isopropyloctane
D)  7-Chloro-5-isopropyl-3,7-dimethyloctaneE) None of the above
F) All of the above

Question 13

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

Question 14

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

Accepted Answer

A)  The reaction involves two steps and occurs fastest with primary alkyl halides.
B)  The reaction involves one step and occurs fastest with primary alkyl halides.
C)  The reaction involves one step and occurs fastest with tertiary alkyl halides.
D)  The reaction involves two steps and occurs fastest with tertiary alkyl halides.E) A) and B)
F) A) and C)

Question 15

Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first.

Accepted Answer

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

Question 16

Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br, (CH3) 2CHCH2Br, CH3CH2CH(CH3) Br, (CH3) 3CBr

Accepted Answer

A)  CH3CH2CH2CH2Br
B)  (CH3) 2CHCH2Br
C)  CH3CH2CH(CH3) Br
D)  (CH3) 3CBrE) A) and B)
F) A) and C)

Question 17

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium hydroxide?

Accepted Answer

A)  1-Iodobutane
B)  1-Chlorobutane
C)  1-Fluorobutane
D)  1-BromobutaneE) A) and B)
F) All of the above

Question 18

Which of the following statements is not true?

Accepted Answer

A)  In polar protic solvents, nucleophilicity decreases down a column of the periodic table as the size of the anion increases.
B)  Nucleophilicity is affected by the solvent used in a substitution reaction.
C)  Polar protic solvents are capable of intermolecular hydrogen bonding.
D)  Polar protic solvents solvate both cations and anions.E) C) and D)
F) None of the above

Question 19

Which of the following alkyl halides is a primary alkyl halide?

Accepted Answer

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

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.E) B) and D)
F) B) and C)

Exam 7: Alkyl Halides and Nucleophilic Substitution

Which of the following structures have the correct common name?

Correct AnswerverifiedShow Answer

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?

Correct AnswerverifiedShow Answer

Which of the following statements about SN2 reactions is true?

Correct AnswerverifiedShow Answer

What is the IUPAC name of the following compound?

Correct AnswerverifiedShow Answer

The reaction of what nucleophile and substrate is represented by the following transition state?

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What is the IUPAC name of the following compound?

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

Correct AnswerverifiedA

What is the starting material in the reaction shown below?

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Rank the following compounds in order of increasing SN1 reactivity?

Correct AnswerverifiedShow Answer

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?

Correct AnswerverifiedShow Answer

What is the IUPAC name of the following compound?

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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 statements about an SN1 reaction mechanism is true?

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Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first.

Correct AnswerverifiedC

Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br, (CH3) 2CHCH2Br, CH3CH2CH(CH3) Br, (CH3) 3CBr

Correct AnswerverifiedShow Answer

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium hydroxide?

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Which of the following statements is not true?

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Which of the following alkyl halides is a primary alkyl halide?

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Which of the following statements is true?

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Which of the following statements about S_N2 reactions is true?

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Which of the following rate laws describes the kinetics of an S_N1 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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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 an S_N1 reaction mechanism is true?

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C

Which of the following alkyl halides would react the fastest with H₂O in S_N1 reaction? CH₃CH₂CH₂CH₂Br, (CH₃) ₂CHCH₂Br, CH₃CH₂CH(CH₃) Br, (CH₃) ₃CBr

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Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium hydroxide?

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A

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