Question

(i) Why phenol has a higher boiling point than toluene?
(ii) Why alcohols are easily protonated but phenol is not protonated?

Answer 1

$\left(i\right)$ In phenol, $-OH$ group is present as a functional group which is highly polar in nature. Due to this, phenol is associated with strong hydrogen bonds. Considerable amount of energy is required to be supplied to boil phenol.
In toluene, hydrogen bonding is absent. Hence it has low boiling point than phenol.
$\left(ii\right)$ The lone pair, on oxygen is not readily available for protanation due to resonance stabilization in phenol. Hence, protonation is difficult.
In alcohols, there is no resonance, hence protonation is facilitated.