Acidity and reactions of phenols

Why this is asked: Phenol is more acidic than an alcohol because the phenoxide ion delocalises its negative charge into the ring by resonance, but it's still far less acidic than a carboxylic acid, whose carboxylate spreads over two equivalent oxygens instead. An electron-withdrawing group at the ortho or para position (like NO₂) raises phenol's acidity further; an electron-donating one (CH₃, OCH₃) lowers it — ranking substituted phenols by acidity is a recurring question type.

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