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Exam 22: Reactions of Benzene and Its Derivatives

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Question 51

Multiple Choice

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

A) 1
B) 2
C) 3
D) 4

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

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Question 52

Multiple Choice

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

A) Bimolecular nucleophilic substitution (S_N2)
B) Nucleophilic aromatic substitution by elimination-addition
C) Nucleophilic aromatic substitution by addition-elimination
D) Electrophilic aromatic substitution

E) C) and D)
F) B) and C)

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Question 53

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

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

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

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

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

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

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

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)?

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

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

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

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

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.

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

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

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

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

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 ______.