Chapter 22, Problem 36P

Interpretation Introduction

Interpretation:

Thestructure of the product formed by reaction of aniline with each of the given reagent is to be predicted.

Concept introduction:

The aryl amines are weak bases that can abstract proton from a strong acid and form their conjugate acids.

The primary amine, on reaction with excess of primary alkyl halide, undergoes nucleophilic substitution and forms quaternary ammonium salt.

The primary amine can be converted to an amide by the reaction with acyl chloride or acid anhydride.

The nucleophilic addition of primary amine to the carbonyl group of aldehyde or ketone forms an imine. The imine, on catalytic hydrogenation, forms a secondary amine.

The aryl diazonium salt is a key intermediate in synthesis of aromatic compounds, which is prepared by nitrosation of amine (primary aryl amine) by sodium nitrite in acidic condition.