Treatment of phenol with cold dilute nitric acid gives

Options

A. `2,4-`dinitrophenol
B. `2,4,6-`trinitrophenol
C. `o-`and`-p-`nitrophenol
D. `m-`nitrophenol

Answer

C

Explanation

We get a mixture of `o-`and `p-`nitrophenols, the former predonminating. Oxidation products are also obtained:
The isomeric products are readily separated by steam distillation. Solubility in hydroxylic solvents such as water depends on (among other things) the power to form hydrogen bonds with the solvant. phenol can form these bonds and hence a certain solubility in water is there. same is true for substitute phenols since the hydroxyl group is still present, but in the `o`-compounds hydrogen bonding with the solvent water molecules is hindered (because chelation is possible) and hence solubility is lowered. Since chelation causes the `o-`compound to behave as a 'monomer', this isomer will be more volatile than the corresponding `m-`and `p-`isomers. Thus the effects of chelation are lower solubility and greater volatility in the `o-`compounds, thus enabling these to be separated from their `m-`and `p-`isomers by steam distillatio.