Why does phenol have a different pH than ethanol, rubbing alcohol, and cyclohexanol?
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Answer:
The aromatic ring is an electron withdrawing group which means it pulls electron density towards it, the electron density can be delocalized throughout the aromatic ring as a result of its aromatic character. This in turn pulls electron density away from the H on the OH attached to the ring giving the H a more positive character and thus a lower pKa. The phenolic anion is said to be resonace stabilized.
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