(a) (i) Why is the $$\mathrm{C}-\mathrm{O}$$ bond length in phenols less than that in methanol?

(ii) Arrange the following in order of increasing boiling point:

Ethoxyethane, Butanal, Butanol, n-butane

(iii) How can phenol be prepared from anisole? Give reaction.

OR

(b) (i) Give mechanism of the following reaction:

$$\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{OH} \xrightarrow[413 \mathrm{~K}]{\mathrm{H}_2 \mathrm{SO}_4} \mathrm{CH}_3 \mathrm{CH}_2-\mathrm{O} -\mathrm{CH}_2 \mathrm{CH}_3+\mathrm{H}_2 \mathrm{O}$$

(ii) Illustrate hydroboration - oxidation reaction with an example.