Question 1

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

Accepted Answer

A)   CH3CºO+
B)   CH3+
C)   CH3CO2-
D)   benzeneE) B) and C)
F) None of the above A

Question 2

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

Accepted Answer

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

Question 3

Provide the structure (a single resonance contributor) of the key intermediate in the following reaction.

Accepted Answer

The answer of Provide the structure (a single resonance contributor)...

Question 4

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

Accepted Answer

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

Question 5

What type of intermediate is formed in the reaction between bromobenzene and sodium amide to give aniline?

Accepted Answer

A)   Meisenheimer complex
B)   benzyne
C)   cyclohexadienyl cation
D)   benzyl radicalE) A) and D)
F) All of the above

Question 6

Which of the following chlorobenzenes does not undergo nucleophilic aromatic substitution upon treatment with NaNH2? 2?   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) A) and B)
F) A) and C)

Question 7

Which mechanism accounts for the reaction of 4-bromotoluene with sodium amide to form a mixture of 3- and 4-aminotoluene?

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

Question 8

Which of the following substituents is ortho/para directing and deactivating in electrophilic aromatic substitution reactions?

Accepted Answer

A)   COCH3
B)   NH3
C)   Br
D)   CH2CH3E) C) and D)
F) A) and B)

Question 9

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 C)
F) B) and C)

Question 10

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

Accepted Answer

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

Question 11

What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl3 to give 4-chloro-1-tert-butylbenzene?

Accepted Answer

A)   Meisenheimer complex
B)   benzyne
C)   cyclohexadienyl cation
D)   benzyl radicalE) B) and C)
F) B) and D)

Question 12

Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-toluene with sodium amide?

Accepted Answer

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

Question 13

Which of the following undergoes the most rapid sulfonation upon treatment with fuming sulfuric acid?

Accepted Answer

A)   benzene
B)   benzoic acid
C)   benzonitrile
D)   nitrobenzeneE) A) and C)
F) B) and C)

Question 14

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

Accepted Answer

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

Question 15

Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?

Accepted Answer

A)   Cl, CN, NO2
B)   Cl, NH2, CH3
C)   CH3, OCH3, COCH3
D)   CH3, NH2, OCH3E) B) and C)
F) A) and D)

Question 16

Which of the following is the reactive intermediate formed in the electrophilic Friedel-Crafts acylation of toluene with CH3COCl and AlCl3? 3COCl and AlCl3?   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) B) and D)
F) None of the above

Question 17

Which of the following reactions or sequences will provide 1-propylbenzene as the major product?

Accepted Answer

A)   treatment of benzene with isopropyl alcohol and HF
B)   treatment of benzene with propanoyl chloride and AlCl3; followed by reaction with Zn(Hg)  and HCl
C)   treatment of benzene with 1-chloropropane and AlCl3
D)   treatment of benzene with 1-propene and HFE) None of the above
F) B) and C)

Question 18

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

Accepted Answer

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

Question 19

What is the role of FeBr3 in electrophilic aromatic bromination of benzene using Br2?

Accepted Answer

A)   nucleophile
B)   electrophile
C)   Lewis acid
D)   baseE) B) and C)
F) A) and D)

Question 20

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) C) and D)

Exam 22: Reactions of Benzene and Its Derivatives

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

Correct AnswerverifiedA

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

Correct AnswerverifiedB

Provide the structure (a single resonance contributor) of the key intermediate in the following reaction.

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What type of intermediate is formed in the reaction between bromobenzene and sodium amide to give aniline?

Correct AnswerverifiedShow Answer

Which of the following chlorobenzenes does not undergo nucleophilic aromatic substitution upon treatment with NaNH2?

Correct AnswerverifiedShow Answer

Which mechanism accounts for the reaction of 4-bromotoluene with sodium amide to form a mixture of 3- and 4-aminotoluene?

Correct AnswerverifiedB

Which of the following substituents is ortho/para directing and deactivating in electrophilic aromatic substitution reactions?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl3 to give 4-chloro-1-tert-butylbenzene?

Correct AnswerverifiedShow Answer

Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-toluene with sodium amide?

Correct AnswerverifiedShow Answer

Which of the following undergoes the most rapid sulfonation upon treatment with fuming sulfuric acid?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?

Correct AnswerverifiedShow Answer

Which of the following is the reactive intermediate formed in the electrophilic Friedel-Crafts acylation of toluene with CH3COCl and AlCl3?

Correct AnswerverifiedShow Answer

Which of the following reactions or sequences will provide 1-propylbenzene as the major product?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What is the role of FeBr3 in electrophilic aromatic bromination of benzene using Br2?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

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

Correct Answer
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A

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B

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Which of the following chlorobenzenes does not undergo nucleophilic aromatic substitution upon treatment with NaNH₂?

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B

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What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl₃ to give 4-chloro-1-tert-butylbenzene?

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Which of the following is the reactive intermediate formed in the electrophilic Friedel-Crafts acylation of toluene with CH₃COCl and AlCl₃?

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What is the role of FeBr₃ in electrophilic aromatic bromination of benzene using Br₂?

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