Chapter 9, Problem 9.84P

Interpretation Introduction

(a)

Interpretation:

It is to be suggested why the given reaction will not occur as indicated.

Concept introduction:

Protonation of ether coverts ether to a good leaving group.

Interpretation Introduction

(b)

Interpretation:

It is to be suggested why the given reaction will not occur as indicated.

Concept introduction:

A strong nucleophile with an aprotic solvent favors ${\text{S}}_{\text{N}}\text{2}$ reaction. In an ${\text{S}}_{\text{N}}\text{2}$ reaction, the nucleophile attacks the substrate only from the side opposite the leaving group, backside attack. The substituents that remain on the atom being attacked undergo Walden inversion.

Interpretation Introduction

(c)

Interpretation:

It is to be suggested why the given reaction will not occur as indicated.

Concept introduction:

Strong base favors deprotonation instead of substitution reaction.

Interpretation Introduction

(d)

Interpretation:

It is to be suggested why the given reaction will not occur as indicated.

Concept introduction:

An alkoxide anion is the strong base and can deprotonate the solvent to form a strong nucleophile.