(a) How do you convert the following?
(i) Phenol to Anisole
(ii) Ethanol to Propan-2-ol
(b) Write mechanism of the following reaction:

(c) Why phenol undergoes electrophilic substitution more easily than benzene?

OR

(a) Account for the following:
(i) o-nitrophenol is more steam volatile than p-nitrophenol.
(ii) t-butyl chloride on heating with sodium methoxide gives 2-methylpropene instead of t-butylmethylether.
(b) Write the reaction involved in the following:
(i) Reimer-Tiemann reaction
(ii) Friedal-Crafts Alkylation of Phenol
(c) Give simple chemical test to distinguish between Ethanol and Phenol.

(a) (i)
$\left(\mathrm{ii}\right) {\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{OH}\underset{∆}{\overset{\mathrm{PCC}}{\to }}{\mathrm{CH}}_3\mathrm{CHO}\underset{{\mathrm{H}}^{+}}{\overset{{\mathrm{CH}}_3\mathrm{MgBr}}{\to }}{\mathrm{CH}}_3-\mathrm{CH}\left(\mathrm{OH}\right)-{\mathrm{CH}}_3$
(b) Mechanism:

(c) Phenol has lone pair on oxygen. It delocalizes on the ring making the ring electron rich due to which, electrophilic substitution reaction occurs easy than Benzene.

OR

(a) (i) In o-nitrophenol there is intramolecular hydrogen bonding due to which it is more steam volatile. In p-nitrophenol there is intermolecular hydrogen bonding which holds molecules together more strongly making it less steam volatile.

(ii) Tertiary cation and strong base Favours elimination reaction. t-butyl cation is formed as intermediate in this reaction. As methoxide ion is a strong base it favors elimination giving 2-methoxy as major product.

(b)

(c) Phenol is an unsaturated aromatic alcohol, while ethanol is saturated aliphatic alcohol. Ethanol reacts with triodomethane (iodoform test) and forms yellow precipitate, while phenol does not give this test. Phenol has benzene ring it under goes diazo coupling reaction, while ethanol doesn't give this test.