Exam 17: Reactions of Aromatic Compounds

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

Provide the major organic product of the following reaction.

Provide the structure of the major organic product(s) in the following reaction.

Provide a detailed, stepwise mechanism for the following reaction.

Provide a series of synthetic steps by which p-methylanisole can be prepared from p-cresol.

Provide the major organic product that results when benzene is treated with the following sequence of reagents: 1. HNO₃, H₂SO₄ 2. Br₂, FeBr₃.

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

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

Provide the major organic product of the following reaction.

Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E⁺.

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

Provide the structure of the most stable resonance form of the intermediate that yields p-bromoanisole when anisole is treated with Br₂/FeBr₃.

Provide the major organic product of the following reaction.

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

Which of the following species is attacked by benzene in the electrophilic nitration reaction?

Provide the major organic product of the following reaction.

In electrophilic aromatic substitution reactions, a -CO₂H substituent on the aromatic ring is:

Rank the following sigma complexes in order of increasing stability.

Which of the following is an intermediate when 1,2-dibromo-4-nitrobenzene is heated with NaOH in a nucleophilic aromatic substitution reaction?

Which of the following compounds will not undergo Friedel-Crafts acylation when treated with