Chapter 11, Problem 11.46SP

(a)

Interpretation Introduction

Interpretation:

The conversion of $\left(S\right)\text{-hexan-2-ol}$ into the given compound is to be stated.

Concept introduction:

Thionyl chloride in dioxane ${\text{SOCl}}_{\text{2}}/\text{dioxane}$ converts alcohols into alkyl chloride selectively through retention of configuration.

(b)

Interpretation Introduction

Interpretation:

The conversion of $\left(S\right)\text{-hexan-2-ol}$ into the given compound is to be stated.

Concept introduction:

Phosphorous bromide $\left({\text{PBr}}_3\right)$ is used to convert alcohols into alkyl halide through inversion of configuration.

(c)

Interpretation Introduction

Interpretation:

The conversion of $\left(S\right)\text{-hexan-2-ol}$ into the given compound is to be stated.

Concept introduction:

The conversion of $\left(S\right)\text{-hexan-2-ol}$ into $\left(R\right)\text{-hexane-2-ol}$ is done by the formation of tosylate ester, that is good leaving group, and elimination of leaving group $\left({}^{-}\text{OTs}\right)$ through ${\text{S}}_{\text{N}}2$ mechanism.