Chapter 24.9, Problem 10P

Interpretation Introduction

Interpretation:

The most stable conformation of chloromethyl methyl ether is to be sketched.

Concept introduction:

The gauche conformation for structural units of the type $\text{X}-\text{C}-\text{Y}-\text{R}$ is more stable than its anti-conformation due to anomeric effect. The $\text{X}$ and $\text{Y}$ mentioned in the structure are electronegative atoms. $\text{Y}$ must have at least one unshared lone pair of electrons.

The anomeric effect in this case describes that the heteroatom $\text{X}$ orients in a way that the $\text{C}-\text{X}$ and $\text{Y}-\text{R}$ bonds are in gauche conformation instead of less hindered anti conformation.