Chapter 22, Problem 22.20P

Interpretation Introduction

Interpretation:

The synthesis of N-phenylbenzamide from benzene as the only starting material is to be proposed.

Concept introduction:

Electrophilic addition reactions finish benzene’s aromaticity forever. Electrophilic aromatic substitution reactions grant the permission to incorporate lots of substituents onto an aromatic ring, however, most of the substituent cannot be put in place directly to the aromatic ring. To incorporate these kinds of the substituents on the benzene ring by first using electrophilic aromatic substituents reaction to incorporate different substituents that are subsequently transformed into the desired product. A Friedel–Crafts acylation of benzene is carried out with acyl chloride and lewis acid., which yield an aromatic ketone, in which C atom from benzene form a bond to the carbon atom of the acyl group.

For incorporate an amino group into a ring needs a substituent attached on the aromatic ring is attached by a carbon atom. This requires the benzylic carbon to be bonded at least one hydrogen atom. Further, this nitro group can be transformed into an amino group. This reduction can be carried out either by catalytic hydrogenation under acidic conditions followed by treatment with $\text{NaOH}$ to neutralize the acid.