Chapter 19.SE, Problem 73AP

Interpretation Introduction

Interpretation:

The observation that the S_N² reaction of (dibromomethyl) benzene with NaOH yields benzaldehyde rather than (dihydroxymethyl) benzene is to be explained.

Concept introduction:

Gem dihalides when treated with bases undergo S_N² reaction to yield gem diols. Gems diols being unstable, as they have two –OH groups on the same carbon, eliminate a molecule of water to yield a carbonyl compound as the product.

To explain:

The observation that the S_N² reaction of (dibromomethyl) benzene with NaOH yields benzaldehyde rather than (dihydroxymethyl) benzene.