Question

Q. 12.10. An organic compound with the molecular
formula C,H,90 forms 2,4-DNP derivative, reduces Tollens'
reagent and undergoes Cannizzaro reaction. On vigorous
oxidation, it gives 1,2-benzenedicarboxylic acid. Identify the
compound.
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Answer 1

$\huge\textcolor{orange}{\texttt{Answer :-}}$

The given compound forms 2,4-DNP derivative. Therefore, it is an aldehyde or ketone. Since it reduces Tollen's reagent, it must be an aldehyde. The compound undergoes Cannizzaro's reaction, so it does not contain $\alpha-$hydrogen.

On vigorous oxidation, it gives 1,2-benzendicarboxylic acid, it means that it must be containing an alkyl group at 2-position with respect to —CHO group on the benzene ring.