Chapter 11.14, Problem 11.35P

(a)

Interpretation Introduction

To determine: The enantiomer of $\text{2-ethoxybutane}$ that has been obtained and an explanation for the path to synthesize $\text{2-ethoxybutane}$ from the ${\text{S}}_{\text{N}}2$ reaction of ethyl tosylate with $\text{sodium}\left(S\right)\text{-but-2-oxide}$.

Interpretation: The enantiomer of $\text{2-ethoxybutane}$ that has been obtained and an explanation for the path to synthesize $\text{2-ethoxybutane}$ from the ${\text{S}}_{\text{N}}2$ reaction of ethyl tosylate with $\text{sodium}\left(S\right)\text{-but-2-oxide}$ is to be stated.

Concept introduction: The Williamson ether synthesis involves displacement of an alkyl halide or tosylate by an alkoxide ion through ${\text{S}}_{\text{N}}2$ mechanism and inversion of configuration. Thus, it likely to be works when alkyl halide or tosylate is less hindered and alkoxide is more hindered.

(b)

Interpretation Introduction

To determine: The best synthesis path for $\left(R\right)\text{-2-ethoxybutane}$.

Interpretation: The best synthesis path for $\left(R\right)\text{-2-ethoxybutane}$.is to be stated.

Concept introduction: The Williamson ether synthesis involves ${\text{S}}_{\text{N}}2$ displacement with inversion of configuration and by this it yields an excellent amount of product.

(c)

Interpretation Introduction

To determine: The conversion of $\left(S\right)\text{-butane-2-ol}$ to $\left(R\right)\text{-2-ethoxybutane}$.

Interpretation: The conversion of $\left(S\right)\text{-butane-2-ol}$ to $\left(R\right)\text{-2-ethoxybutane}$ is to be stated.

Concept introduction: The Williamson ether synthesis involves ${\text{S}}_{\text{N}}2$ displacement with inversion of configuration and by this it yields an excellent amount of product.