Question
Tue February 19, 2013 By:

Phenol are more acidic than aliphatic alcohals. WHY

Expert Reply
Tue February 19, 2013

The phenoxide ion is stabilized by the electron-withdrawing effect of the aromatic ring system. Resonance stabilization of the phenoxide ion, lowers the PE of the products of the ionization, decreases the ?H, and shifts the equilibrium farther to the right, making phenol more acidic than an alcohol.  Aliphatic alcohols ionize to a lesser extent because the alkoxide ion is relatively less stable, so they are less acidic.

Ask the Expert