Chapter 13.20, Problem 28P

Interpretation Introduction

Interpretation:

The canonical structure of cyclohexadienyl anion that is associated with the lowest energy and is formed during the reaction of methoxide ion with $\text{o}-\text{fluoronitrobenzene}$ is to be determined.

Concept Introduction:

Nucleophilic aromatic substitution reactions involve the substitution of a leaving group by an upcoming nucleophile.

The aromatic ring is itself act as a nucleophile, hence the ring undergoes this substitution only in the presence of a strong electron withdrawing so that it stabilized the negative charge on the ring.