19. Reactions of Aromatics: EAS and Beyond

Suggest reagents and reaction conditions that would result in synthesis of the following bromoalkanes.

(c)

Predict the product of the following benzylic bromination reactions.

(c)

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

c.

Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below. In each case, explain what unwanted reactions might produce undesirable impurities in the product.

Show the products you expect when each compound reacts with NBS with light shining on the reaction.

(d)

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)

Predict the product of the following benzylic bromination reactions.

(a)

A radical reaction, as it progressed through its propagation steps, involved the following radical species. Suggest which products might form in all possible termination steps (six products are possible).