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Question -

An organic compound with the molecularformula C9H10O forms 2, 4-DNP derivative, reduces Tollens’ reagent andundergoes Cannizzaro reaction.



Answer -

 On vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid. Identify the compound.


Answer

It is given that the compound (withmolecular 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 onoxidation gives 1, 2-benzenedicarboxylic acid. Therefore, the −CHO group is directlyattached to a benzene ring and this benzaldehyde is ortho-substituted. Hence,the compound is 2-ethylbenzaldehyde.

The given reactions can be explained by the followingequations.

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