Given reasons for the following:

A. Protonation of Phenols is difficult whereas ethanol easily undergoes protonation.

B. Boiling point of ethanol is higher than that of dimethyl ether.

C. Anisole on reaction with HI gives phenol and as main products and not iodobenzene and

a) In phenols, the lone pairs of electrons, on the oxygen atom are delocalized over the benzene ring due to the resonance and hence are not easily available for protonation.

In contrast in alcohols, the lone pairs of electrons on the oxygen ato are localized due to the absence of resonance and hence are easily available for protonation.

b) The boiling point of ethanol (CH₃CH₂OH) is higher because it ca form intermolecular Hydrogen-bonding.

In contrast in dimethyl-ether, there is hydrogen-bonding possible and hence has low boiling point.

c) Anisole on reaction with HI gives phenol and CH₃—I as main products

In anisole, O-bond is stronger to resonance, and as a result dissociation of O-bond with benzene becomes difficult and hence, phenol and methyl iodide is formed.