Chapter 19, Problem 19.64P

Interpretation Introduction

Interpretation:

The missing intermediates and reagents in the given synthesis are to be supplied.

Concept introduction:

A is the alcohol product from a reduction reaction of an aldehyde and ${\text{LiAlH}}_{\text{4}}$. The alcohol is then converted to alkyl bromide which reacts with $\text{Mg}\left(\text{s}\right)\text{/ether}$ to form Grignard reagent, B. A benzyl group is added to alter the carbon skeleton, and the identity of C is $\text{benzaldehyde}$ (source of electrophilic carbon). Another benzyl group is added to form $\text{benzylic ether}$ in a Williamson ether synthesis, and the identity of D is $\text{benzyl bromide}$ (source of electrophilic carbon).