* Resonance stabilization of the phenoxide ion: When phenol loses a proton, the resulting phenoxide ion is stabilized by resonance. The negative charge can be delocalized across the aromatic ring, making the ion more stable.
* Inductive effect: The electronegative oxygen atom in phenol withdraws electron density from the carbon atom holding the hydroxyl group, making it more acidic. This inductive effect is less pronounced in 1-hexanol.
In contrast:
* 1-hexanol is a simple alcohol. The alkoxide ion formed by deprotonation is not stabilized by resonance or significant inductive effects.
Therefore, the phenoxide ion is significantly more stable than the 1-hexanol alkoxide ion, making phenol a stronger acid.