Chapter 10.7, Problem 29P

(a)

Interpretation Introduction

Interpretation:

The given compound should be synthesized from 3,3-dimethyl-l-butene.

${\text{S}}_{\text{N}}\text{1}$reaction:

In the nucleophilic substitution reaction, the rate of reaction depends only on one reactant, which is involved in reaction is called unimolecular nucleophilic substitution reaction.

In ${\text{S}}_{\text{N}}\text{1}$ reaction, formation of carbocation by reliving of leaving group from reactant is the first step and second step is addition nucleophile to carbocation.

The rate determination step is formation of carbocation.

The stability order of carbocation is,

Tertiary > Secondary > Primary

Therefore, 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 undergoes ${\text{S}}_{\text{N}}\text{1}$ substitution reaction.

(b)

Interpretation Introduction

Interpretation:

The given compound should be synthesized from 3,3-dimethyl-l-butene.

Concept introduction:

Meta chloro perbenzoic acid is reaction with alkene which forms the epoxide.

Lithium aluminium hydride is used as a reducing agent.

Lithium aluminium hydride is reduced the epoxide as an alcohol which is shown below.

Epoxides are reactive molecules.