Oxidation of phenol with chromic acid produces benzoquinone. In the presence of air, phenols undergo slow oxidation, forming dark-colored mixtures containing quinones.
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Phenoxide ion, produced by treating phenol with sodium hydroxide, undergoes electrophilic substitution with carbon dioxide in Kolbe’s reaction, forming ortho hydroxybenzoic acid as the main product. The phenoxide ion is more reactive than phenol due to its enhanced nucleophilicity.