19. Reactions of Aromatics: EAS and Beyond

Predict the major products of treating the following compounds with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

(a) isopropylbenzene

(b) p-xylene

(c)

What is the major product of the following reactions? Disregard stereoisomers:

c.

What are the products of the following reactions?

c.

Predict the major products of the following reactions.

(f) p-methylanisole + Br₂ , light

A halogenation intended to make compound A formed B instead.

(d) Without looking it up, would you expect C–H_a or C–H_b to have the lower bond-dissociation energy?

A halogenation intended to make compound A formed B instead.

(b) Suggest a mechanism that rationalizes the formation of B.

Predict the product of the following benzylic bromination reactions.

(a)