Chapter 23, Problem 23.79P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern mechanism of the reaction. The substituent ring with deactivating group precedes the reaction through benzyne intermediate formation. Methyl groups deactivate the ring towards nucleophilic addition reaction.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Interpretation Introduction

(c)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.