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Exam 22: Reactions of Benzene and Its Derivatives

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Question 31

Multiple Choice

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

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

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

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Question 32

Multiple Choice

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

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 HF

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

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Question 33

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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)?

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

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 ______.

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

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)?

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

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 ________________________.

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

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 _____.

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

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

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

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

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

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

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

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

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