Chapter 16.SE, Problem 68AP

Interpretation Introduction

Interpretation:

A mechanism for the reaction of 1-chloroanthraquinone with methoxide ion to give the substitution product 1-methoxyanthraquinone is to be proposed using curved arrows to show the electron flow in each step.

Concept introduction:

Aryl halides that have electron-withdrawing groups undergo nucleophilic substitution reactions. The nucleophile first attacks the electron deficient aryl halide to form a resonance-stabilized, negatively charged intermediate, called Meisenheimer complex which then eliminates a halide ion to yield the product.

To propose:

Using curved arrows to show the electron flow in each step, a mechanism for the reaction of 1-chloroanthraquinone with methoxide ion to give the substitution product 1-methoxyanthraquinone.