Chapter 17, Problem 44PP

Interpretation Introduction

Interpretation: For the given compound, major product should be predicted when it is treated with Birch condition and the mechanism for its formation should be proposed.

Concept introduction:

• Birch reduction converts aromatic compound having benzoid ring in to a product 1, 4-cyclohexa diene. The product having hydrogen atoms attached on opposite end of the molecule
• Birch reduction is the reduction of aromatic rings with sodium, potassium or lithium and an alcohol in liquid ammonia. Birch reduction is unlike catalytic hydrogenation
• When benzene with an electron donating group such as alkyl group is treated with Birch reduction, the carbon atom connected to the alkyl group is not reduced. Electron   donating effect destabilizes the radical anion.
• When an electron withdrawing groups are used, different regiochemical outcome is observed. Electron withdrawing   effect stabilizes the intermediate.