Why are phenols considered to be more acidic than alcohols and water?

Reasons for high acidity of phenols:
1. The hydroxyl group attached to the sp2hybridised carbon of benzene ring which acts as an electron
withdrawing group. Due to the higher electronegativity of sp2 hybridised carbon of phenol to
which –OH is attached, electron density decreases on oxygen. This increases the polarity of O–H
bond and results in an increase in ionization of phenols than that of alcohols.
2. High polarity of phenols due to charge distributions via resonance within the ring. Alcohols do not
undergo resonance.
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3. Resonance stabilization of phenoxide ion: The phenoxide ion is more stable than a typical alkoxide
ion because the negative charge is not confined to the oxygen atom but is delocalized over the
oxygen and three carbon atoms of the ring.
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