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Exam 17: Reactions of Aromatic Compounds

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Question 61

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Draw the four major resonance structures of the intermediate which results when is treated with NaOH.

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Question 62

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In electrophilic aromatic substitution reactions, the -CF₃ group is ________.

A) an activating group because it donates electron density through inductive stabilization
B) an activating group because it donates electron density through resonance
C) a deactivating group because it withdraws electron density through inductive destabilization
D) a deactivating group because it withdraws electron density through resonance

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

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Question 63

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Rank the following groups in order of increasing activating power in electrophilic aromatic substitution reactions: -Br.

What sequence of reagents is needed to convert benzene into m-bromoethylbenzene?

Electrophilic iodination of benzene requires which reagent in addition to I₂?

Provide the structures of the major organic products of the following reaction.

In the addition of an electrophile to acetophenone, which of the following best describes the expected mode of reaction?

Which step in an electrophilic aromatic substitution reaction is typically rate determining, formation of the sigma complex or loss of H⁺ by the sigma complex to form the product? Explain.

Provide the structure of the major organic product in the following reaction sequence.

Which of the following is the best choice of reagents to effect the electrophilic iodination of an aromatic ring?

Provide the major organic product(s) of the reaction shown below.

Provide the structure of the major mononitration product(s) of the compound below.

The nitration of anisole ________.

Derivatives of the compound shown below are currently being examined for their effectiveness in treating drug addiction and metabolic syndrome (J. Med. Chem. 2006, 872) . Which sequence ranks the following aromatic rings of this compound in order of increasing reactivity in an electrophilic aromatic substitution reaction (slowest to fastest reacting) ?

Provide a detailed, stepwise mechanism for the following reaction.

Provide a series of synthetic steps by which p-nitrobutylbenzene can be prepared from benzene.

Provide the structure of the major mononitration product of the compound below.

Complete the following reaction by filling in the necessary reagents.

Provide the major organic product of the following reaction.

Provide the structures of the major organic products of the following reaction.