(a) An organic compound (A) with the molecular formula $\mathrm{C}_9 \mathrm{H}_{10} \mathrm{O}$ forms 2, 4-DNP derivative, reduces Fehling solution and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2-benzene dicarboxylic acid.

(i) Identify the compound (A) and write its IUPAC name.

(ii) Write the reaction of compound (A) with

(1) 2,4-Dinitrophenyl hydrazine and

(2) Fehling solution

(iii) Write the equation of compound (A) when it undergoes Cannizzaro reaction.

OR

(b) (i) Account for the following:

(1) The alpha ( $\alpha$ )-hydrogens of aldehydes and ketones are acidic in nature.

(2) Oxidation of aldehydes is easier than ketones.

(ii) Arrange the following in :

(1) Decreasing reactivity towards nucleophilic addition reaction propanal, acetone, benzaldehyde.

(2) Increasing order of boiling point: Propane, Ethanol, Dimethylether, Propanal

(iii) Give simple chemical test to distinguish between Benzoic acid and Benzaldehyde.