19. Reactions of Aromatics: EAS and Beyond

Propose products (if any) and mechanisms for the following AlCl₃-catalyzed reactions:

(a) chlorocyclohexane with benzene

Predict the products.

(a) <IMAGE>

(b) <IMAGE>

Propose products (if any) and mechanisms for the following AlCl3-catalyzed reactions:

(b) methyl chloride with anisole

Predict the major products formed when benzene reacts (just once) with the following reagents.

(a) tert-butyl bromide, AlCl3

(b) 1-chlorobutane, AlCl3

Predict the major products formed when benzene reacts (just once) with the following reagents.

(c) isobutyl alcohol + BF3

Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with the following reagents.

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(d) isobutylene and HF

Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with the following reagents.

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(e) cyclohexanol and BF₃

For each reaction, show the generation of the electrophile and predict the products.

(c) tert-butylbenzene + 2-methylpropene + HF

For each reaction, show the generation of the electrophile and predict the products.

(d) propan-2-ol + toluene + BF₃