Chapter 23, Problem 23.12YT

Interpretation Introduction

Interpretation:

The nucleophilic addition of ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{NH}}_{\text{2}}$ to $\text{1-chloro-4-nitrobenzene}$ produces the given Meisenheimer complex. The additional resonance structures of the intermediate are to be drawn. The most stable resonance structure is to be determined, and the reason is to be explained.

Concept introduction:

The lone pair of electrons adjacent to a separate $\text{π}$ bond can be moved to get a new resonance structure. The uncharged ${\text{sp}}^{\text{3}}$-hybridized C atom cannot be involved in resonance. The negative charge on the most electronegative atom makes the resonance structure most stable.