Chapter 13.12, Problem 25ATS

Interpretation Introduction

Interpretation:

The structure of the compound (2) has to be drawn and the mechanism for the conversion of compound (1) to (3) has to be determined.

Concept Introduction:

Williamson ether synthesis: A reaction to converts alcohols $\left(\text{R-OH}\right)$ into ethers $\left(\text{R-O-R}\right)\text{.}$ First step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by using strong base. This reaction forms hydrogen gas $\left({\text{H}}_{\text{2}}\right)$ as a byproduct. The deprotonated alcohol will react with an alkyl halide to form ether.

When using the alkyl halides, methyl halide and primary alkyl halides are the best because of the less steric hindrance. Tertiary alkyl halides will fails in Williamson ether synthesis because of the steric hindrance.