Question 1

Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol?

Accepted Answer

A)   1
B)   2
C)   3
D)   4E) A) and B)
F) A) and C)

Question 2

Which of the following is the most nucleophilic?

Accepted Answer

A)   sodium ethoxide
B)   acetic acid
C)   methanol
D)   waterE) None of the above
F) C) and D)

Question 3

What is(are)  the major organic product(s)  obtained from the following substitution reaction?

Accepted Answer

A)   only 1
B)   only 2
C)   only 1 and 2
D)   1, 2 and 3E) A) and B)
F) A) and D)

Question 4

Which of the following sets consists of only polar aprotic solvents?

Accepted Answer

A)   water, hexane, methanol
B)   acetic acid, DMF, toluene
C)   DMSO, ethanol, acetonitrile
D)   DMF, acetonitrile, DMSOE) All of the above
F) C) and D)

Question 5

Arrange the following in decreasing order of their nucleophilicity. CH3CH2CH2Li, CF3CH2CH2O−, CH3CH2CH2O−, CH3CH2CH2S−

Accepted Answer

A)   CH3CH2CH2Li > CH3CH2CH2S− > CH3CH2CH2O− > CF3CH2CH2O−
B)   CH3CH2CH2S− > CH3CH2CH2O− > CF3CH2CH2O− > CH3CH2CH2Li
C)   CH3CH2CH2Li > CF3CH2CH2O− > CH3CH2CH2O− > CH3CH2CH2S−
D)   CF3CH2CH2O− > CH3CH2CH2O− > CH3CH2CH2S− > CH3CH2CH2LiE) All of the above
F) B) and C)

Question 6

Which of the following anions is the best leaving group in an SN1 reaction?

Accepted Answer

A)   F−
B)   HO−
C)   NH2−
D)   Cl−E) A) and D)
F) C) and D)

Question 7

Which of the following alkyl bromides reacts the slowest with NaSCH3 in DMF? 3 in DMF?   A)  1 B)  2 C)  3 D)  4" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   1
B)   2
C)   3
D)   4E) B) and D)
F) B) and C)

Question 8

Which of the following statements is true regarding the reaction of tert-butyl bromide with water?

Accepted Answer

A)   the rate is proportional to the concentration of tert-butyl bromide
B)   the rate is proportional to the concentration of water
C)   the rate is independent of the identity of the solvent
D)   the rate of the reaction is independent of the temperatureE) A) and D)
F) All of the above

Question 9

Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?

Accepted Answer

A)   dimethylsulfoxide
B)   water
C)   hexane
D)   toluene, PhCH3E) A) and B)
F) A) and C)

Question 10

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 11

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 12

What is(are)  the major organic product(s)  obtained from the following substitution reaction?

Accepted Answer

A)   only 1
B)   only 2
C)   only 1 and 2
D)   1, 2 and 3E) A) and B)
F) B) and C)

Question 13

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe?

Accepted Answer

A)   methyl iodide
B)   ethyl iodide
C)   2-bromopropane
D)   tert-butyl chlorideE) B) and D)
F) A) and D)

Question 14

Which of the following reactions corresponds to a substitution?

Accepted Answer

A)   tert-butanol → tert-butyl chloride
B)   tert-butanol → 2-methylpropene
C)   3,3-dimethyl-2-butanol → 2,3-dimethyl-2-butene
D)   cyclohexene → 1,2-dichlorocyclohexaneE) All of the above
F) None of the above

Question 15

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 16

Which of the following energy diagrams represents the course of an exothermic SN2 reaction? N2 reaction?   A)  1 B)  2 C)  3 D)  4" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   1
B)   2
C)   3
D)   4E) A) and B)
F) A) and C)

Question 17

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

Accepted Answer

The reaction proceeds in a sin...

Question 18

Identify the major product of the following reaction. ​

Accepted Answer

A)  
B)  
C)  
D)  E) All of the above
F) B) and C)

Question 19

Identify the major product of the following reaction. ​

Accepted Answer

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

Question 20

What is the major organic product obtained from the following reaction?

Accepted Answer

A)   1
B)   2
C)   3
D)   4E) All of the above
F) None of the above

Exam 9: Nucleophilic Substitution and Beta-Elimination

Which of the following sets consists of only polar aprotic solvents?

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Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium methylthiolate, NaSMe?

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Which of the following anions is the best leaving group in an SN1 reaction?

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Which of the following is the most nucleophilic?

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Arrange the following in decreasing order of their nucleophilicity. CH3CH2CH2Li, CF3CH2CH2O−, CH3CH2CH2O−, CH3CH2CH2S−

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Which of the following energy diagrams represents the course of an exothermic SN2 reaction?

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What is(are) the major organic product(s) obtained from the following substitution reaction?

Correct AnswerverifiedShow Answer

What is(are) the major organic product(s) obtained from the following substitution reaction?

Correct AnswerverifiedShow Answer

Identify the major product of the following reaction. ​

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Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?

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What is the major organic product obtained from the following reaction?

Correct AnswerverifiedShow Answer

Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl bromide and methanol?

Correct AnswerverifiedShow Answer

Which of the following reactions corresponds to a substitution?

Correct AnswerverifiedShow Answer

Identify the major product of the following reaction. ​

Correct AnswerverifiedShow Answer

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

Correct AnswerverifiedThe reaction proceeds in a sin...View AnswerShow Answer

What is the major organic product obtained from the following reaction?

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Which of the following statements is true regarding the reaction of tert-butyl bromide with water?

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Which of the following alkyl bromides reacts the slowest with NaSCH3 in DMF?

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What is the major organic product obtained from the following reaction?

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What is the major organic product obtained from the following reaction?

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Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium methylthiolate, NaSMe?

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Which of the following anions is the best leaving group in an S_N1 reaction?

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Arrange the following in decreasing order of their nucleophilicity. CH₃CH₂CH₂Li, CF₃CH₂CH₂O−, CH₃CH₂CH₂O−, CH₃CH₂CH₂S−

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Which of the following energy diagrams represents the course of an exothermic S_N2 reaction?

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Identify the major product of the following reaction.

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Identify the major product of the following reaction.

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The reaction proceeds in a sin...
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Correct Answer
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Which of the following alkyl bromides reacts the slowest with NaSCH₃ in DMF?

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Correct Answer
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