Which one among alcohols and phenols are more acidic and why?

Asked by Topperlearning User | 7th Jun, 2016, 03:12: PM

Expert Answer:

Phenoxide is better stabilized than phenol as it carries only a negative charge and phenol has a strong tendency to form more stable phenoxide ion by the release of proton.

But, in case of alcohol both the alcohol molecule and the alkoxide ion are represented by one structure each and there is no resonance.
Also the alkoxide ion due to presence of a formal negative charge has greater energy and is less stable than the alcohol molecule.Thus alcohol have negligible tendency to form less stable alkoxide ion by releasing a proton.
 
Thus Phenols are stronger acids than alcohol   because in case of phenol the phenoxide ion left after the release of a proton is stabilized by resonance.

Answered by  | 7th Jun, 2016, 05:12: PM