Question

An organic compound with the molecular formula $C_9H_{10}$O 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 $C_9H_{10}O$)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 $1,2-benzenedicarboxylic$ acid.Therefore,the$-CHO$ group is directly attached to a benzene ring and this benzaldehyde is ortho-substituted.Hence,the compound is $2-ethylbenzaldehyde.$

The given reactions can be explained by the following equations.