Chapter 18.SE, Problem 52AP

Interpretation Introduction

Interpretation:

The structure and stereochemistry of the alcohol that would result if 1, 2-epoxycyclohexane was reduced with Lithium aluminium deuteride are to be shown.

Concept introduction:

The nucleophilic attack of the deuderide ion on the epoxide will yield an alcohol. The attack takes places by S_N² like backside attack. When both epoxide carbons are either primary or secondary the nucleophilic attack mainly occurs at the less highly substituted side. When one of the epoxide carbons is tertiary, the nucleophilic attack mainly occurs at the more highly substituted side.

To give:

The structure and stereochemistry of the alcohol that would result if 1, 2-epoxycyclohexane was reduced with Lithium aluminium deuteride.