Chapter 21, Problem 37P

Interpretation Introduction

Interpretation:

In case of halogen-substituted azulenes, a halogen atom on $\text{C6}$ can be displaced by nucleophiles, while one on $\text{C1}$ is unreactive toward nucleophiles. The difference in this behavior is to be discussed.

Concept introduction:

An aromatic compound is more stable than nonaromatic and antiaromatic compounds.

Resonance is the delocalization of the electrons within a molecule.

Nucleophiles are negatively charged species that donate electron pair(s) to electrophile(s) to form a covalent bond.

Nucleophilic aromatic substitution reaction is based on the addition–elimination mechanism.