Question 1

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

Question 2

Which of the following anions is the best leaving group in an SN1 reaction?

Accepted Answer

A)   F-
B)   HO-
C)   NH2-
D)   Cl-E) All of the above
F) None of the above D

Question 3

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

Accepted Answer

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

Question 4

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) All of the above B

Question 5

In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest?

Accepted Answer

A)   acetic acid
B)   ethanol
C)   water
D)   acetonitrileE) None of the above
F) A) and B)

Question 6

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

Accepted Answer

A)   only 1
B)   only 2
C)   only 1 and 2
D)   1, 2 and 3E) All of the above
F) None of the above

Question 7

Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH?

Accepted Answer

A)   tert-butyl fluoride
B)   tert-butyl chloride
C)   tert-butyl bromide
D)   tert-butyl iodideE) B) and C)
F) C) and D)

Question 8

Which of the following energy diagrams represents the course of an exothermic SN1 reaction? N1 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) All of the above
F) A) and B)

Question 9

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

Question 10

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

Accepted Answer

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

Question 11

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

Question 12

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

Question 13

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 three steps:
1....

Question 14

Which of the following is the most nucleophilic?

Accepted Answer

A)   sodium ethoxide
B)   acetic acid
C)   methanol
D)   waterE) A) and B)
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

Which of the following most favors elimination rather substitution in a reaction with 2-bromopropane?

Accepted Answer

A)   sodium methoxide
B)   sodium ethoxide
C)   sodium isoproxide
D)   sodium tert-butoxideE) A) and B)
F) None of the above

Question 17

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

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

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

Accepted Answer

A)   3-methyl-1-pentyne
B)   3-methyl-2-pentyne
C)   1-propene + propyne
D)   4-methyl-2-penteneE) B) and D)
F) All of the above

Question 20

Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?

Accepted Answer

A)   dimethylsulfoxide
B)   water
C)   hexane
D)   toluene, PhCH3E) All of the above
F) C) and D)

Exam 9: Nucleophilic Substitution and Beta-Elimination

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 anions is the best leaving group in an SN1 reaction?

Correct AnswerverifiedD

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedB

In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN3, proceed the fastest?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following alkyl halides undergoes the fastest solvolysis reaction with formic acid, HCOOH?

Correct AnswerverifiedShow Answer

Which of the following energy diagrams represents the course of an exothermic SN1 reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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 three steps:1....View AnswerShow Answer

Which of the following is the most nucleophilic?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following most favors elimination rather substitution in a reaction with 2-bromopropane?

Correct AnswerverifiedShow Answer

Which of the following reactions corresponds to a substitution?

Correct AnswerverifiedD

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?

Correct AnswerverifiedShow Answer

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Which of the following anions is the best leaving group in an S_N1 reaction?

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D

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B

In which of the following solvents would the reaction of 1-bromobutane with sodium azide, NaN₃, proceed the fastest?

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Which of the following energy diagrams represents the course of an exothermic S_N1 reaction?

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

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The reaction proceeds in three steps:
1....
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D

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