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Phenols are aromatic compounds bearing a hydroxyl group directly attached to a benzene ring (Ar–OH). They are more acidic than aliphatic alcohols and readily undergo electrophilic aromatic substitution.
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In phenols, conjugation between the oxygen lone pairs and the aromatic π system stabilizes the phenoxide anion, lowering pK_a values typically to ~9–11 (vs. ~16–18 for simple alcohols). This resonance delocalization also increases electron density at the ortho and para positions, strongly activating the ring toward electrophilic aromatic substitution (halogenation, nitration, sulfonation, Friedel–Crafts-type reactions) and directing substitution to o/p sites. Phenols form robust hydrogen bonds and display higher boiling points than comparable hydrocarbons. They are synthesized industrially via the cumene process, or in the lab by hydrolysis of diazonium salts, cleavage of aryl ethers, or oxidation of alkylbenzenes followed by rearrangement. Oxidation of phenols can yield quinones, important redox-active motifs in biology and materials. Phenolic O-alkylation and O-acylation produce aryl ethers and esters, while deprotonation gives phenoxides that are strong nucleophiles in Williamson ether syntheses. In IR, phenols show broad O–H stretches (~3200–3600 cm⁻¹) and aromatic C=C bands; ¹H NMR typically places the phenolic proton downfield and exchangeable.