Chapter 19, Problem 19.21P

Interpretation Introduction

(a)

Interpretation:

It is to be shown whether the given synthesis can be carried out without protecting the hydroxyl group.

Concept introduction:

A Williamson ether synthesis is the method of ether synthesis in which the alkyl halide is treated with an alkoxide ion. To protect an alcoholic group, it is converted to its silyl ether derivatives like OTBDMS, which is stable under the basic condition or through other protecting groups.

Interpretation Introduction

(b)

Interpretation:

Which other protecting groups from the Table $\text{19-2}$ can be used instead in the given reaction to be explained.

Concept introduction:

To protect an alcoholic group, it is converted to its silyl ether derivatives like OTBDMS, which is stable under the basic condition or through other protecting groups. Other methods to protect the alcoholic group are to form its MOM ether, which is carried out by treating the alcoholic group with corresponding halide of the MOM group under the strong basic condition. The corresponding ether is formed via Williamson ether synthesis.