Question

Protonation of Phenols is difficult whereas ethanol easily undergoes protonation.

Answer 1

Ans: In phenol the lone pair of electrons on Oxygen involves in delocalization not available freely for the protonation. Whereas in alcohols, the electrons on Oxygen atom are not delocalized, so they available for protonation.
As ethanol is also alcohol.

Answer 2

In protonation, the lone pair on the oxygen atom is given to the proton. In the case of phenol, the lone pair of electrons is in conjugation with the benzene ring. Hence they are less available for giving to the proton. In ethanol, the lone pair of electrons on oxygen is not in conjugation. on the other hand, the +I effect of the ethyl group increases the electron density of oxygen. that's why ethanol undergoes protonation easily as compared to phenol.