Question 1

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 B)
F) B) and D)

Question 2

HCl is the electrophile in the following reaction.

Accepted Answer

A) True 
 B)False

Question 3

Which of the following represents the transition state of the rate-determining step in the reaction between 2-bromopropane and sodium methoxide leading to elimination?

Accepted Answer

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

Question 4

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

Accepted Answer

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

Question 5

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) All of the above
F) A) and B)

Question 6

The reaction of tert-butyl bromide, (CH3) 3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3) 3COCH3. What is the effect of doubling the concentration of methanol 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) 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

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

Question 9

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 B)
F) A) and C)

Question 10

In the following reaction the cyanide ion is both a nucleophile and a Lewis acid.

Accepted Answer

A) True 
 B)False

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) A) and C)

Question 12

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

Accepted Answer

A)   water, DMF, DMSO
B)   acetic acid, methanol, water
C)   DMSO, ethanol, acetonitrile
D)   DMF, acetonitrile, DMSOE) None of the above
F) B) and C)

Question 13

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

Question 14

Which of the following statements is not true regarding SN1 reactions?

Accepted Answer

A)   A carbocation intermediate is formed.
B)   The mechanism has only one step.
C)   Polar, protic solvents are good choices for SN1 reactions.
D)   The stereochemical outcome is racemization at the carbon bearing the leaving group.E) A) and C)
F) B) and C)

Question 15

Which of the following is best set of conditions for the preparation of tert-butanol?

Accepted Answer

A)   tert-butyl fluoride in water
B)   tert-butyl bromide in water
C)   tert-butyl fluoride and NaOH in DMSO
D)   tert-butyl bromide and NaOH in DMSOE) A) and B)
F) A) and C)

Question 16

The first step in the mechanism for the following reaction would be the formation of a secondary carbocation.

Accepted Answer

A) True 
 B)False

Question 17

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

Accepted Answer

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

Question 18

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) A) and C)

Question 19

Which of the following energy diagrams represents the course of an exothermic E1 reaction?

Accepted Answer

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

Question 20

What is the major product formed upon treatment of (R)  1-bromo-4-methylhexane with sodium cyanide?

Accepted Answer

A)   (R)  1-cyano-4-methylhexane
B)   (S)  1-cyano-4-methylhexane
C)   (R)  4-methyl-1-hexene
D)   (S)  4-methyl-1-hexeneE) A) and B)
F) A) and C)

Exam 9: Nucleophilic Substitution and Beta-Elimination

Which of the following represents the transition state of the rate-determining step in the reaction between 2-bromopropane and sodium methoxide leading to elimination?

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

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In the following reaction the cyanide ion is both a nucleophile and a Lewis acid.

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Which of the following energy diagrams represents the course of an exothermic E1 reaction?

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

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What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide?

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HCl is the electrophile in the following reaction.

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

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The first step in the mechanism for the following reaction would be the formation of a secondary carbocation.

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

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The reaction of tert-butyl bromide, (CH3) 3CBr, with methanol in an inert solvent proceeds by an SN1 mechanism to give tert-butyl methyl ether, (CH3) 3COCH3. What is the effect of doubling the concentration of methanol on the rate of the reaction?

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

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Which of the following statements is not true regarding SN1 reactions?

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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?

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

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

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

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Which of the following is best set of conditions for the preparation of tert-butanol?

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

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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 is not a characteristic of S_N2 reactions?

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The reaction of tert-butyl bromide, (CH₃) ₃CBr, with methanol in an inert solvent proceeds by an S_N1 mechanism to give tert-butyl methyl ether, (CH₃) ₃COCH₃. What is the effect of doubling the concentration of methanol on the rate of the reaction?

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Which of the following statements is not true regarding S_N1 reactions?

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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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