Question 1

Which of the following compounds undergoes the most rapid nucleophilic substitution with hydroxide ion?

Accepted Answer

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

Question 2

Consider the following compounds.     Use the number of the compound to answer the following question. Place the number in the blank provided.
-The compound that is the least reactive to nitration is ______.

Accepted Answer

The answer of Consider the following compounds.   ...

Question 3

Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?

Accepted Answer

A)  benzene
B)  nitrobenzene
C)  bromobenzene
D)  anisoleE) A) and C)
F) A) and B)

Question 4

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) B) and D)

Question 5

The best sequence in which to carry out the following reaction is 1) Br2, AlBr3, 2) H2SO4, SO3.

Accepted Answer

A) True 
 B)False

Question 6

Which mechanism accounts for the reaction of benzyl chloride with sodium cyanide to form cyanomethylbenzene (phenylacetonitrile, PhCH2CN) ?

Accepted Answer

A)  Bimolecular nucleophilic substitution (SN2) 
B)  Nucleophilic aromatic substitution by elimination-addition
C)  Nucleophilic aromatic substitution by addition-elimination
D)  Electrophilic aromatic substitutionE) A) and B)
F) A) and C)

Question 7

Why does nitrobenzene fail to undergo Friedel-Crafts alkylation with tert-butyl chloride and AlCl3?

Accepted Answer

A)  nitrobenzene reacts with AlCl3
B)  nitrobenzene is a poor nucleophile
C)  the nitro group is a strong electron donating group
D)  the tert-butyl cation is a poor electrophileE) B) and D)
F) A) and B)

Question 8

What is the major organic product obtained from the following sequence of reactions (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)?

Accepted Answer

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

Question 9

Which mechanism accounts for the reaction of 4-bromo-1-nitrobenzene with sodium hydroxide to form 4-nitrophenol?

Accepted Answer

A)  Bimolecular nucleophilic substitution (SN2) 
B)  Nucleophilic aromatic substitution by elimination-addition
C)  Nucleophilic aromatic substitution by addition-elimination
D)  Electrophilic aromatic substitutionE) A) and D)
F) A) and C)

Question 10

Which of the following undergoes the most rapid nitration upon treatment with HNO3/H2SO4?

Accepted Answer

A)  toluene
B)  benzene
C)  bromobenzene
D)  nitrobenzeneE) B) and C)
F) A) and C)

Question 11

What is the major organic product obtained from the following sequence of reactions?

Accepted Answer

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

Question 12

The product of the following reaction would be 2-nitrotoluene.

Accepted Answer

A) True 
 B)False

Question 13

Consider the reaction below to answer the following question(s).  Fill in the blank with the appropriate letter or response.
-This reaction proceeds _____ (faster or slower) than when benzene is used.

Accepted Answer

The answer of Consider the reaction below to answer the...

Question 14

What is the electrophile in the reaction of benzene with acetyl chloride, CH3COCl, and AlCl3?

Accepted Answer

A)  CH3C ≡\equiv≡ O+
B)  CH3+
C)  CH3CO2-
D)  benzene E) All of the above
F) B) and C)

Question 15

Which of the following cannot be prepared from benzene in two synthetic steps?

Accepted Answer

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

Question 16

The electrophile that could be used to make acetophenone (methyl phenyl ketone) from benzene is shown below.

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

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 obtained from the following sequence of reactions?

Accepted Answer

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

Question 20

The predominant intermediate in the electrophilic nitration of toluene is shown below.

Accepted Answer

A) True 
 B)False

Exam 22: Reactions of Benzene and Its Derivatives

Why does nitrobenzene fail to undergo Friedel-Crafts alkylation with tert-butyl chloride and AlCl3?

Correct AnswerverifiedShow Answer

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

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What is the major organic product obtained from the following sequence of reactions?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Consider the following compounds. Use the number of the compound to answer the following question. Place the number in the blank provided. -The compound that is the least reactive to nitration is ______.

Correct AnswerverifiedShow Answer

The electrophile that could be used to make acetophenone (methyl phenyl ketone) from benzene is shown below.

Correct AnswerverifiedShow Answer

Which of the following cannot be prepared from benzene in two synthetic steps?

Correct AnswerverifiedShow Answer

What is the major organic product obtained from the following sequence of reactions (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)?

Correct AnswerverifiedShow Answer

What is the major organic product obtained from the following sequence of reactions?

Correct AnswerverifiedShow Answer

Consider the reaction below to answer the following question(s). Fill in the blank with the appropriate letter or response. -This reaction proceeds _____ (faster or slower) than when benzene is used.

Correct AnswerverifiedShow Answer

Which of the following undergoes the most rapid nitration upon treatment with HNO3/H2SO4?

Correct AnswerverifiedShow Answer

Which of the following compounds undergoes the most rapid nucleophilic substitution with hydroxide ion?

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

Correct AnswerverifiedShow Answer

Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?

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Which mechanism accounts for the reaction of benzyl chloride with sodium cyanide to form cyanomethylbenzene (phenylacetonitrile, PhCH2CN) ?

Correct AnswerverifiedShow Answer

The predominant intermediate in the electrophilic nitration of toluene is shown below.

Correct AnswerverifiedShow Answer

What is the electrophile in the reaction of benzene with acetyl chloride, CH3COCl, and AlCl3?

Correct AnswerverifiedShow Answer

Which mechanism accounts for the reaction of 4-bromo-1-nitrobenzene with sodium hydroxide to form 4-nitrophenol?

Correct AnswerverifiedShow Answer

The best sequence in which to carry out the following reaction is 1) Br2, AlBr3, 2) H2SO4, SO3.

Correct AnswerverifiedShow Answer

The product of the following reaction would be 2-nitrotoluene.

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Why does nitrobenzene fail to undergo Friedel-Crafts alkylation with tert-butyl chloride and AlCl₃?

Correct Answer
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Which of the following undergoes the most rapid nitration upon treatment with HNO₃/H₂SO₄?

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Which of the following undergoes the most rapid bromination upon treatment with Br₂/FeBr₃?

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Which mechanism accounts for the reaction of benzyl chloride with sodium cyanide to form cyanomethylbenzene (phenylacetonitrile, PhCH₂CN) ?

Correct Answer
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What is the electrophile in the reaction of benzene with acetyl chloride, CH₃COCl, and AlCl₃?

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The best sequence in which to carry out the following reaction is 1) Br₂, AlBr₃, 2) H₂SO₄, SO₃.

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