Question 1

The following reaction would have a faster rate in a higher polarity solvent than one of low polarity.

Accepted Answer

A) True 
 B)False

Question 2

What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr)  with water by an SN1 mechanism?

Accepted Answer

A)   Rate = k [t-BuBr]
B)   Rate = k [t-BuBr][H2O]
C)   Rate = k [H2O]
D)   Rate = k [t-BuBr]2E) A) and B)
F) None of the above

Question 3

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 4

Which of the following statements related to SN1 reactions is not true?

Accepted Answer

A)   The SN1 reaction can be described as a heterolytic bond cleavage followed by nucleophilic attack
B)   Carbocations are electrophilic
C)   The charged carbon atom of a carbocation has an unfilled valence shell
D)   Nucleophiles are Lewis acidsE) A) and C)
F) A) and D)

Question 5

Which of the following reactions corresponds to a substitution?

Accepted Answer

A)   propene → 1,2-dibromopropane
B)   1-iodopropane → propene
C)   propene → propane
D)   1-iodopropane → 1-bromopropaneE) B) and D)
F) None of the above

Question 6

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

Accepted Answer

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

Question 7

The following energy diagram could represent an SN2 reaction.

Accepted Answer

A) True 
 B)False

Question 8

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

Question 9

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

Question 10

Why is cyclohexylamine more reactive than aniline when the former reacts with methyl bromide?

Accepted Answer

-NH₂ is a poor leaving group, but it is a...

Question 11

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

Accepted Answer

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

Question 12

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium cyanide, NaCN?

Accepted Answer

A)   methyl iodide
B)   ethyl iodide
C)   2-iodopropane
D)   tert-butyl iodideE) None of the above
F) All of the above

Question 13

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 three steps:
1....

Question 14

Explain Walden inversion.

Accepted Answer

During an aliphatic nucleophilic substit...

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

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

Accepted Answer

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

Question 17

Which of the following energy diagrams represents the course of an exothermic E2 reaction?

Accepted Answer

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

Question 18

The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 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) B) and C)
F) None of the above

Question 19

Which of the following is the best set of conditions for the preparation of tert-butyl methyl ether?

Accepted Answer

A)   tert-butyl fluoride and NaOCH3 in CH3OH
B)   methanol and sodium tert-butoxide in tert-butanol
C)   fluoromethane and sodium tert-butoxide in tert-butanol
D)   tert-butyl bromide and CH3OHE) All of the above
F) None of the above

Question 20

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

Accepted Answer

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

Exam 9: Nucleophilic Substitution and Beta-Elimination

Which of the following energy diagrams represents the course of an exothermic E2 reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following reactions corresponds to a substitution?

Correct AnswerverifiedShow Answer

Explain Walden inversion.

Correct AnswerverifiedDuring an aliphatic nucleophilic substit...View AnswerShow Answer

Which of the following statements related to SN1 reactions is not true?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an SN1 mechanism?

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 three steps:1....View AnswerShow Answer

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?

Correct AnswerverifiedShow Answer

The reaction of methyl iodide with sodium azide, NaN3, proceeds by an SN2 mechanism. What is the effect of doubling the concentration of NaN3 on the rate of the reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

The following reaction would have a faster rate in a higher polarity solvent than one of low polarity.

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Why is cyclohexylamine more reactive than aniline when the former reacts with methyl bromide?

Correct Answerverified-NH2 is a poor leaving group, but it is a...View AnswerShow Answer

The following energy diagram could represent an SN2 reaction.

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following is the best set of conditions for the preparation of tert-butyl methyl ether?

Correct AnswerverifiedShow Answer

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium cyanide, NaCN?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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During an aliphatic nucleophilic substit...
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Which of the following statements related to S_N1 reactions is not true?

Correct Answer
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What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr) with water by an S_N1 mechanism?

Correct Answer
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Correct Answer
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The reaction proceeds in three steps:
1....
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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?

Correct Answer
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The reaction of methyl iodide with sodium azide, NaN₃, proceeds by an S_N2 mechanism. What is the effect of doubling the concentration of NaN₃ on the rate of the reaction?

Correct Answer
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Correct Answer
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Correct Answer
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Correct Answer
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-NH₂ is a poor leaving group, but it is a...
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The following energy diagram could represent an S_N2 reaction.

Correct Answer
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Correct Answer
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Correct Answer
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Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium cyanide, NaCN?

Correct Answer
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Correct Answer
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