Question 1

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

Question 2

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 3

Which of the following is most likely to undergo rearrangement during reaction with methanol?

Accepted Answer

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

Question 4

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

Accepted Answer

A)   F-
B)   Cl-
C)   Br-
D)   I-E) A) and B)
F) All of the above

Question 5

Which of the following is the best leaving group in an SN2 reaction?

Accepted Answer

A)   F-
B)   H3C-
C)   CH3O2SO-
D)   HO-E) B) and C)
F) All of the above

Question 6

Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl iodide and water leading to elimination?

Accepted Answer

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

Question 7

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

Question 8

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) A) and B)

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 organic product obtained from the following reaction?

Accepted Answer

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

Question 11

What is the best choice of reagent to perform the following transformation? 2SO4 B)  H2O C)  NaOCH3 D)  KOtBu" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   H2SO4
B)   H2O
C)   NaOCH3
D)   KOtBuE) All of the above
F) A) and D)

Question 12

Which of the following represents the transition state of the reaction between methyl iodide and ammonia?

Accepted Answer

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

Question 13

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

Question 14

Which of the following is not a characteristic of SN2 reactions?

Accepted Answer

A)   the electrophilic carbon undergoes inversion of stereochemistry
B)   the rate is proportional to the concentration of substrate
C)   the rate is proportional to the concentration of nucleophile
D)   the rate is independent of the solventE) A) and D)
F) A) and C)

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

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

Question 17

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

Accepted Answer

A)   only 1
B)   only 2
C)   only 3
D)   a mixture of 1 and 2E) A) and D)
F) A) and C)

Question 18

What is the equation for the rate of formation of 2-methoxypropane, (CH3CH(OCH3) CH3, from the reaction of 2-bromopropane (i-PrBr)  with sodium methoxide (NaOCH3) ?

Accepted Answer

A)   Rate = k [i-PrBr]
B)   Rate = k [i-PrBr]2
C)   Rate = k [NaOCH3]
D)   Rate = k [i-PrBr][NaOCH3]E) None of the above
F) A) and B)

Question 19

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

Accepted Answer

A)   1-hexyne
B)   2-hexyne
C)   propene + propyne
D)   propane + propyneE) B) and C)
F) A) and B)

Question 20

The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of doubling the concentration of NaI 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 B)
F) A) and C)

Exam 9: Nucleophilic Substitution and Beta-Elimination

What is the best choice of reagent to perform the following transformation?

Correct AnswerverifiedShow Answer

Which of the following is not a characteristic of SN2 reactions?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following represents the transition state of the reaction between methyl iodide and ammonia?

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

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

What is the equation for the rate of formation of 2-methoxypropane, (CH3CH(OCH3) CH3, from the reaction of 2-bromopropane (i-PrBr) with sodium methoxide (NaOCH3) ?

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 anions is the most nucleophilic in polar aprotic solvents?

Correct AnswerverifiedShow Answer

Which of the following is most likely to undergo rearrangement during reaction with methanol?

Correct AnswerverifiedShow Answer

What is the major organic product obtained from the following 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

Which of the following represents the transition state of the rate-determining step in the reaction between tert-butyl iodide and water leading to elimination?

Correct AnswerverifiedShow Answer

The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of doubling the concentration of NaI on the rate of the reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following is the best leaving group in an SN2 reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Correct Answer
verified

Which of the following is not a characteristic of S_N2 reactions?

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

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
verified

Correct Answer
verified

Correct Answer
verified

What is the equation for the rate of formation of 2-methoxypropane, (CH₃CH(OCH₃) CH₃, from the reaction of 2-bromopropane (i-PrBr) with sodium methoxide (NaOCH₃) ?

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

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
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Which of the following is the best leaving group in an S_N2 reaction?

Correct Answer
verified

Correct Answer
verified