Chapter 11.SE, Problem 32MP

Interpretation Introduction

Interpretation:

The reason has to be explained for the given compound does not undergo a nucleophilic substitution reaction by either S_N1 or S_N2 mechanisms.

Concept introduction:

S_N1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation. Primary alcohol is less stable therefore it won’t undergo S_N1 substitution reaction.

S_N2 reaction:

Tosylated compound is reaction with sodium methoxide which undergoes again S_N2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

Given information:

The given compound is shown below,