Exam 17: Reactions of Aromatic Compounds

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

Which of the following compounds undergoes reaction with HNO₃/H₂SO₄ at the fastest rate?

Which of the following compounds will undergo bromination most rapidly using Br₂, FeBr₃?

What type of reaction is shown below? (Org. Lett., 2013, 15 (15), 3950-3953)

Draw the major organic structure that results from the following sequence of reactions.

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

Draw the three major resonance structures of the sigma complex intermediate in the reaction of acetophenone with HNO₃/H₂SO₄ to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

Provide a series of synthetic steps by which 3-bromoethylbenzene can be prepared from benzene.

Provide a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene.

Which of the following compounds would most likely be used in the preparation of isobutylbenzene from benzene?

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

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

Provide the major organic product of the following reaction sequence.

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction.

Name the major organic product which results when 3-ethylbenzenesulfonic acid is heated in aqueous acid.

In electrophilic aromatic substitution reactions the hydroxyl group is an o,p-director because ________.

When 2,4-dinitrochlorobenzene is treated with sodium hydroxide at 100°C followed by protonation ________.

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