Chapter 17, Problem 47DSP

Interpretation Introduction

Interpretation:

The location of the deuterium in the isobutyl alcohol product prepared by the reduction of $\text{1, 2-Epoxy-2-methylpropane}$ using ${\text{LiAlD}}_{\text{4}}{\text{/AlCl}}_{\text{3}}$ is to be determined.

Concept introduction:

Rearrangements occur during epoxide opening reactions.

The epoxide oxygen is either protonated or coordinated to a Lewis acid.

One of the groups attached to the carbon atom migrates, eventually producing an aldehyde or ketone.

${\text{LiAlH}}_{\text{4}}$ is a reducing agent and reduces aldehydes and ketone by donation of a hydride ion to the carbonyl carbon.

An aldehyde is reduced to a primary alcohol while a ketone is reduced to a secondary alcohol.