Question 1

Which of the following is not a characteristic of SN1 reactions?

Accepted Answer

A)   the electrophilic carbon undergoes inversion of stereochemistry
B)   the rate is proportional to the concentration of substrate
C)   the reaction proceeds faster in a more polar solvent
D)   the rate is independent of the concentration of nucleophileE) All of the above
F) A) and B)

Question 2

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

Question 3

Which of the following statements is true regarding the reactivity of 1 and 2 with potassium tert-butoxide?

Accepted Answer

A)   1 reacts faster than 2
B)   1 and 2 give different dehydrochlorinated products
C)   2 reacts by elimination whereas 1 reacts by substitution
D)   1 reacts by elimination whereas 2 reacts by substitutionE) A) and B)
F) All of the above

Question 4

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

Accepted Answer

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

Question 5

Which of the following compounds is the most nucleophilic in polar protic solvents?

Accepted Answer

A)   H2O
B)   NH3
C)   H2S
D)   PH3E) All of the above
F) B) and D)

Question 6

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

Accepted Answer

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

Question 7

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

Accepted Answer

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

Question 8

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

Accepted Answer

The reaction proceeds in a sin...

Question 9

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

Accepted Answer

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

Question 10

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

Accepted Answer

A)   1
B)   2
C)   3
D)   4E) All of the above
F) A) and C)

Question 11

Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH3? 3?   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 D)
F) A) and C)

Question 12

Which of the following statements is not true regarding the SN2 reaction of (R) -2-bromobutane with sodium cyanide?

Accepted Answer

A)   the reaction proceeds with inversion of configuration
B)   the rate is proportional to the concentration of sodium cyanide
C)   the rate is proportional to the concentration of (R) -2-bromobutane
D)   the rate of the reaction is independent of the identity of the solventE) A) and D)
F) A) and C)

Question 13

Which of the following compounds undergoes the most rapid hydrolysis reaction?

Accepted Answer

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

Question 14

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

Accepted Answer

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

Question 15

Which of the following represents the transition state of the rate-determining step in the SN1 reaction between tert-butyl chloride and water? N1 reaction between tert-butyl chloride and water?   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 D)
F) A) and C)

Question 16

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

Accepted Answer

The answer of Draw all of the chloroalkanes that undergo...

Question 17

Which of the following most favors elimination rather substitution in a reaction with sodium methoxide?

Accepted Answer

A)   bromomethane
B)   bromoethane
C)   1-bromopropane
D)   2-bromopropaneE) All of the above
F) A) and B)

Question 18

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

Accepted Answer

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

Question 19

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaN3?

Accepted Answer

A)   1-fluorohexane
B)   1-chlorohexane
C)   1-bromohexane
D)   1-iodohexaneE) A) and B)
F) A) and C)

Question 20

The reaction of tert-butyl chloride, (CH3) 3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3) 3COH. What is the effect of doubling the concentration of water 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 4E) All of the above
F) B) and C)

Exam 9: Nucleophilic Substitution and Beta-Elimination

Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

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Which of the following statements is true regarding the reactivity of 1 and 2 with potassium tert-butoxide?

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

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Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of paris 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 most favors elimination rather substitution in a reaction with sodium methoxide?

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Which of the following compounds is the most nucleophilic in polar protic solvents?

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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 SN2 reaction with sodium azide, NaN3?

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Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH3?

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Which of the following represents the transition state of the rate-determining step in the SN1 reaction between tert-butyl chloride and water?

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

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Which of the following statements is not true regarding the SN2 reaction of (R) -2-bromobutane with sodium cyanide?

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

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The reaction of tert-butyl chloride, (CH3) 3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3) 3COH. What is the effect of doubling the concentration of water on the rate of the reaction?

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

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Which of the following is not a characteristic of SN1 reactions?

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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 compounds undergoes the most rapid hydrolysis reaction?

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

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The reaction proceeds in a sin...
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Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium azide, NaN₃?

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Which of the following represents the transition state of the reaction between methyl bromide and sodium methylthiolate, NaSCH₃?

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Which of the following represents the transition state of the rate-determining step in the S_N1 reaction between tert-butyl chloride and water?

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Which of the following statements is not true regarding the S_N2 reaction of (R) -2-bromobutane with sodium cyanide?

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The reaction of tert-butyl chloride, (CH₃) ₃CCl, with water in an inert solvent gives tert-butyl alcohol, (CH₃) ₃COH. What is the effect of doubling the concentration of water on the rate of the reaction?

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Which of the following is not a characteristic of S_N1 reactions?

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