Question

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

Answer 1

(a) It is an aldehyde or ketone as it forms 2,4-DNP derivative.

(b)As the compound reduces Tollerls reagent and undergoes cannizzaro reaction, it is an aldehyde and not a ketone.

(c) On vigrous oxidation, it gives 1, 2-benzenedicarboxylic acid. So, it must have an alkyl group at o- ortho position with respect to CHO group on the benzene ring.

(d) Molecular formula suggests that it should be 2-ethyl benzaldehyde.