Chapter 25, Problem 25.24P

Interpretation Introduction

Interpretation:

The detailed mechanism for the formation of two isomeric products from the Birch reduction of monosubstituted benzene is to be drawn.

Concept introduction:

The Birch reduction is metal catalyzed single hydrogenation of an aromatic compound where it reduces the benzene ring to $\text{cyclohexa-1, 4-diene}$. It is similar to dissolving metal reduction reaction where a metal is dissolved in a solvent like liquid ammonia except that there is a small amount of alcohol added as a proton source in case of Birch reduction. The reaction proceeds through formation of a radical anion by addition of solvated electron to $\text{π}$ bond.