Anorganic compound with molecular formula `C_9H_10O` forms 2,4-DNP derivative, reduces Tollens' reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid. Identify the compound.

Explanation

Since the given compound with molecular formula `C_(9)H_(10)O` forms a 2,4-DNA derivative and reduces Tollen's reagent, it must be an aldehyde. Since it undergoes Cannizzaro reaction, therefore, CHO group is directly attached to die benzene ring.
Since on vigorous oxidation, it gives 1,2-benzene dicarboxylic acid, therefore, it must be an ortho-substituted benzaldehyde. The only o-substituted aromatic aldehyde haveing molecular formula `C_(9)H_(10)O` is ethyl benzaldehyde. Ail the reactions can now be explained on the basis of this structure.