Question

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.

Answer 1

It is given that the compound (with molecular formula C9H10O) forms 2, 4-DNP derivative and reduces Tollen’s reagent. Therefore, the given compound must be an aldehyde. Again, the compound undergoes cannizzaro reaction and on oxidation gives 1, 2benzenedicarboxylic acid. Therefore, the −CHO group is directly attached to a benzene ring and this benzaldehyde is ortho-substituted. Hence, the compound is
2ethylbenzaldehyde.