Chapter 23, Problem 23.30P

Interpretation Introduction

Interpretation:

The synthesis of $m\text{-(2-methylpropyl)aniline}$ from benzene is to be shown.

Concept introduction:

The aromaticity of the benzene ring disappears during electrophilic addition reactions. Electrophilic aromatic substitution reactions grant permission to incorporate lots of substituents onto an aromatic ring, however, most of the substituents 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 nitration of acylation is carried out with acyl chloride and an acid, which yield a ketone. The nitro group and acetyl group are meta directors. The order in which substitution occurs is important because some substituents on the ring make certain electrophilic reactions unfeasible. The Friedel-Craft acylation as the first step and nitration should be the final step because the benzene ring would be highly deactivated.