Question 1

Which of the following reactions or reaction sequences will not give isopropylbenzene as the major product?

Accepted Answer

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

Question 2

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

Question 3

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) A) and C)

Question 4

Tetracyclone (shown below) is often used to trap benzynes as Diels-Alder adducts.  The structure of the Diels-Alder adduct that results when benzyne is trapped by tetracyclone would be

Accepted Answer

A) True 
 B)False

Question 5

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) None of the above

Question 6

What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

Accepted Answer

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

Question 7

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) All of the above

Question 8

Consider the reaction below to answer the following question(s).  Fill in the blank with the appropriate letter or response.
-The name of product D is ________________________.

Accepted Answer

m-bromonitrobenzene ...

Question 9

Which of the following chlorobenzenes produces a single isomer 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) B) and C)
F) A) and D)

Question 10

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 11

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

Question 12

Which of the following are valid resonance structures of the electophile involved in Friedel-Crafts acylation of benzene upon treatment 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 C)
F) All of the above

Question 13

Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions?

Accepted Answer

A)  Cl, CH3, CN
B)  Br, OH, COCH3
C)  Cl, OH, CH3
D)  CN, NO2, COCH3E) C) and D)
F) A) and B)

Question 14

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

Accepted Answer

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

Question 15

The predominant product from sequential nitration and bromination of benzenesulfonic acid is shown below.

Accepted Answer

A) True 
 B)False

Question 16

Why does anisole undergo bromination with Br2 in the absence of FeBr3 whereas bromination of benzene requires the presence of FeBr3?

Accepted Answer

A)  anisole is a better nucleophile than benzene
B)  the methoxy group of anisole is an inductive electron withdrawing substituent
C)  Br2 is a good nucleophile
D)  the reaction is accelerated by lightE) C) and D)
F) B) and C)

Question 17

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

Question 18

Consider the reaction below to answer the following question(s) .  Fill in the blank with the appropriate letter or response.
-The Lewis acid catalyst in the reaction is _____.

Accepted Answer

A)  A
B)  B
C)  C
D)  DE) B) and C)
F) A) and D)

Question 19

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 most reactive to nitration is ______.

Accepted Answer

The answer of Consider the following compounds.   ...

Question 20

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)...

Exam 22: Reactions of Benzene and Its Derivatives

The predominant product from sequential nitration and bromination of benzenesulfonic acid is shown below.

Correct AnswerverifiedShow Answer

Consider the reaction below to answer the following question(s) . Fill in the blank with the appropriate letter or response. -The Lewis acid catalyst in the reaction is _____.

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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

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 most reactive to nitration is ______.

Correct AnswerverifiedShow Answer

Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions?

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Why does anisole undergo bromination with Br2 in the absence of FeBr3 whereas bromination of benzene requires the presence of FeBr3?

Correct AnswerverifiedShow Answer

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

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

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

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

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

What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

Correct AnswerverifiedShow Answer

Tetracyclone (shown below) is often used to trap benzynes as Diels-Alder adducts. The structure of the Diels-Alder adduct that results when benzyne is trapped by tetracyclone would be

Correct AnswerverifiedShow Answer

Which of the following chlorobenzenes produces a single isomer upon treatment with NaNH2?

Correct AnswerverifiedShow Answer

Which of the following are valid resonance structures of the electophile involved in Friedel-Crafts acylation of benzene upon treatment with CH3COCl and AlCl3?

Correct AnswerverifiedShow Answer

Consider the reaction below to answer the following question(s). Fill in the blank with the appropriate letter or response. -The name of product D is ________________________.

Correct Answerverifiedm-bromonitrobenzene ...View AnswerShow Answer

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

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

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Which of the following reactions or reaction sequences will not give isopropylbenzene as the major product?

Correct AnswerverifiedShow Answer

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Why does anisole undergo bromination with Br₂ in the absence of FeBr₃ whereas bromination of benzene requires the presence of FeBr₃?

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Which of the following chlorobenzenes produces a single isomer upon treatment with NaNH₂?

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Which of the following are valid resonance structures of the electophile involved in Friedel-Crafts acylation of benzene upon treatment with CH₃COCl and AlCl₃?

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m-bromonitrobenzene ...
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