Chapter 13, Problem 48P

Give reagents suitable for carrying out each of the following reactions, and write the major

organic products. If an ortho, para mixture is expected, show both. If the meta isomer is the

expected major product, write only that isomer.

Nitration of nitrobenzene

Bromination of toluene

Bromination of (trifluoromethyl)benzene

Sulfonation of anisole

Sulfonation of acetanilide ()

Chlorination of bromobenzene

Friedel–Crafts alkylation of anisole with benzyl chloride

Friedel–Crafts acylation of benzene with benzoyl chloride ()

Nitration of the product from part (h)

Clemmensen reduction of the product from part (h)

Wolff–Kishner reduction of the product from part (h)