19. Reactions of Aromatics: EAS and Beyond

What is the major product of a Friedel–Crafts alkylation using the following alkyl chlorides?

e. (CH₃)₂CHCH₂Cl

f. CH₂=CHCH₂Cl

Design a synthesis for each of the following, using an intramolecular reaction:

d.

What product is obtained from the reaction of excess benzene with each of the following reagents?

c. dichloromethane + AlCl₃

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

a. chlorocyclohexane with benzene

Predict the products.

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.

(d) isobutylene and HF

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

(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

Predict the product of the following Friedel–Crafts alkylation reactions. Assume only one alkyl group adds in each case.

(d)