Chapter 10.SE, Problem 38AP

Interpretation Introduction

Interpretation:

Given that (S)-3-methylhexane undergoes radical bromination to yield optically inactive 3-bromo-3-methylhexane as the major product. Whether the product and the radical intermediate are chiral or not is to be stated.

Concept introduction:

In the free radicals produced from chiral molecules the carbon bearing the odd electron is in sp²- hybridized state. It has only three bonds around it with the odd electron in the unhydridized p orbital. So it is achiral in nature. When it further reacts, the other radical can attack this radical from both above and below of its plane leading to two different stereoisomers in equal proportions. The product thus will be a racemic mixture.

To state:

The product and the radical intermediate formed when (S)-3-methylhexane undergoes radical bromination to yield optically inactive 3-bromo-3-methylhexane are chiral or not.