Q 14-14-60 E - Organic Chemistry (Mcmurry)

Question

Adiponitrile, a starting material used in the manufacture of nylon, can be prepared in three steps from 1,3-butadiene. How would you carry out this synthesis?

Step-by-Step Solution

Answer

The first step of the three is-

Introduction

Adiponitrile is an organic compound which is a precursor used for polymer nylon. Nylon is a synthetic polymer made up of polyamides. It is a silk like thermoplastic made from petroleum which can be melted, can be processed into fibres, films or shapes.

Addition, Nucleophilic substitution, Catalytic hydrogenation

First step is the addition of on 1,4 positions to form 1,4-dibromo-2-butene.

After this, 1,4-dibromo-2-butene undergoes nucleophilic substitution with NaCN  (SN²)

The product then forms Adiponitrile by undergoing catalytic hydrogenation.