Chapter 9, Problem 9.47P

Interpretation Introduction

(a)

Interpretation: The products formed by the treatment of ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OTs}$ with the given reagent are to be drawn.

Concept introduction: The strong nucleophile, and $1\text{°}$ alkyl tosylate both favors an ${\text{S}}_{\text{N}}\text{2}$ mechanism. The ${\text{S}}_{\text{N}}\text{2}$ mechanism proceeds through backside attack, and results a substitution product.

Interpretation Introduction

(b)

Interpretation: The products formed by the treatment of ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OTs}$ with the given reagent are to be drawn.

Concept introduction: The strong nucleophile, and $1\text{°}$ alkyl tosylate both favors an ${\text{S}}_{\text{N}}\text{2}$ mechanism. The ${\text{S}}_{\text{N}}\text{2}$ mechanism proceeds through backside attack, and results a substitution product.

Interpretation Introduction

(c)

Interpretation: The products formed by the treatment of ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OTs}$ with the given reagent are to be drawn.

Concept introduction: The strong nucleophile, and $1\text{°}$ alkyl tosylate both favors an ${\text{S}}_{\text{N}}\text{2}$ mechanism. The ${\text{S}}_{\text{N}}\text{2}$ mechanism proceeds through backside attack, and results a substitution product.

Interpretation Introduction

(d)

Interpretation: The products formed by the treatment of ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OTs}$ with the given reagent are to be drawn.

Concept introduction: The strong nucleophile, and $1\text{°}$ alkyl tosylate both favors an ${\text{S}}_{\text{N}}\text{2}$ mechanism. The ${\text{S}}_{\text{N}}\text{2}$ mechanism proceeds through backside attack, and results a substitution product. However, with strong nucleophilic bulky bases reaction proceeds through an $\text{E2}$ mechanism and yield elimination products.