32.2.2—Reactions of phenol

Phenol combines the chemistry of an aromatic ring with an –OH group. The hydroxyl group can be deprotonated, while its lone pair also activates the ring towards electrophilic substitution.

Use the reagent to identify which part reacts: bases remove the phenolic proton; bromine or nitric acid substitutes on the ring under phenol-specific conditions.

Phenol reacts with aqueous sodium hydroxide to form sodium phenoxide, and with bromine water to give a 2,4,6-tribrominated product.

Phenol is not simply an alcohol attached to benzene: its acidity and ring reactivity are both altered by conjugation.