Question 1

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 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) B) and D)

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 C)
F) B) and D)

Question 4

All of the following can act as an electrophile in an electrophilic aromatic substitution reaction.
SO3 (CH3)3C+ NO2+

Accepted Answer

A) True 
 B)False

Question 5

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

Accepted Answer

A)   Br, CH3, NO2
B)   CH3, NH2, Br
C)   Cl, OCH3, COCH3
D)   NO2, COCH3, COOHE) A) and C)
F) C) and D)

Question 6

An example of a metal-reducing agent is _____.

Accepted Answer

A)   zinc
B)   xenon
C)   radon
D)   seleniumE) B) and D)
F) C) and D)

Question 7

Identify "X" in the given reaction. ​

Accepted Answer

A)   3-methyl-2-propanol
B)   2-methyl-2-butanol
C)   2-methyl-2-propanol
D)   3-methyl-2-butanolE) All of the above
F) A) and B)

Question 8

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 9

What is the major organic product obtained from the following reaction (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 10

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

Question 11

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

Accepted Answer

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

Question 12

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 D)

Question 13

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

Accepted Answer

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

Question 14

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

Accepted Answer

A)   benzene
B)   nitrobenzene
C)   bromobenzene
D)   anisoleE) B) and D)
F) All of the above

Question 15

Which of the following is not true about benzynes?

Accepted Answer

A)   They are planar
B)   They are formed upon dehydrohalogenation of aryl halides
C)   They are aromatic
D)   They are intermediates in nucleophilic aromatic substitution reaction which take place by an addition-elimination mechanismE) C) and D)
F) A) and B)

Question 16

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

Question 17

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

Question 18

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 19

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

Question 20

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) C) and D)
F) All of the above

Exam 22: Reactions of Benzene and Its Derivatives

Which of the following is not true about benzynes?

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

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

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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

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

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

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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?

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

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

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

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

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

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Identify "X" in the given reaction. ​

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An example of a metal-reducing agent is _____.

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All of the following can act as an electrophile in an electrophilic aromatic substitution reaction. SO3 (CH3)3C+ NO2+

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

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

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

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

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

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Identify "X" in the given reaction.

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All of the following can act as an electrophile in an electrophilic aromatic substitution reaction. SO₃(CH₃)₃C⁺ NO₂⁺

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

Correct Answer
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