An organic compound with the molecular formula C9H10O forms 2,4-DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid. Identify the compound.

Since the given compound with molecular formula C₉H₁₀O form a 2,4-DNP derivative and reduce Tollen’s reagent, it must be an aldehyde. Since it undergoes cannizzaro reaction, therefore CHO group is directly attached to the benzene ring.

Since on vigorous oxidation, it gives 1,2-benzene dicarboxylic acid, therefore it must be ortho-substituted benzaldehyde. The only o-substituted aromatic aldehyde having molecular formula C₉H₁₀O is o—ethyl benzyldehyde all the reaction can show now be explained on the basis of this structure-