Chapter 11, Problem 9PP

Interpretation Introduction

Interpretation:

The structures for the products A, B, C, and D showing stoichiometry are to be written.

Concept Introduction:

For carrying out a nucleophilic substitution on alcohols, first the hydroxyl group of an alcohol gets converted to a good leaving group to a p-toluenesulfonate ester derivative on reaction with p-toluenesulfonyl chloride $\left(TsCl\right)$. This reaction proceed with retention of configuration. Then, in the second step, this ester is allowed to react with a nucleophile like $O{H}^{-}$.

If the mechanism of nucleophilic substitution is $S_{N}2$, then inversion of configuration takes place at the carbon to which alcohol hydroxyl group is attached.

Usually, primary alcohols undergo $S_{N}2$ mechanism. But whether secondary alcohols undergo $S_{N}2$ mechanism or not depends upon the strength of nucleophile.