Question

An organic compound with molecular formula C₉ H₁₀O 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

From the given data it is clear that as the compound forms 2, 4-DNP derivative it has CO group. Since it reduces Tollens’ reagent therefore -CHO group is present. As it can also undergo Cannizzaro reaction therefore α -hydrogen is absent

The oxidation product suggests that the compound has a benzene ring. One of the – COOH groups have been obtained by the oxidation of – CHO group and the other from alkyl group. Hence on these basis, the structure of C₉H₁₀O is