Question 1

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]2

Question 2

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 temperature

Question 3

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 solvent

Question 4

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

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4

Question 5

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

Accepted Answer

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

Question 6

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

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4

Question 7

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

Accepted Answer

A)  F- 
B)  H3C- 
C)  CH3O2SO- 
D)  HO-

Question 8

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 2

Question 9

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 4

Question 10

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]

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 the major organic product obtained from the following reaction?

Accepted Answer

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

Question 13

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)  4

Question 14

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 + propyne

Question 15

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 4

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

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

Accepted Answer

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

Question 18

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 19

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)  4

Question 20

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

Accepted Answer

A)  H2SO4 
B)  H2O 
C)  NaOCH3 
D)  KOtBu

Exam 9: Nucleophilic Substitution and Beta-Elimination

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?

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

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

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

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

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

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

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

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?

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) ?

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

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

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

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

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?

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

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

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

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?

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

Exam 9: Nucleophilic Substitution and Beta-Elimination

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?

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

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

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

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

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

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

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

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?

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) ?

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

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

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

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

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?

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

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

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

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?

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

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?

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

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

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?

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) ?