Question

An organic compound with molecular formula C₉H₁₀O forms 2,4-DNP derivative, reduces Tollen’s reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1,2-benzenedicarboxylic acid. Identify the compound.

Answer 1

The compound forms 2,4-DNP derivative. It shows that it is a carbonyl compound. Further it reduces Tollens’ reagent which shows that it contains aldehydic group. It undergoes Cannizzaro reaction indicating that aldehyde group is without any α-hydrogen. On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid which shows that there are two carbon residues on benzene ring. Since the molecular formula is C₉H₁₀O, it fits into the structure, 2-ethylbenzaldehyde.