Question

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

Answer 1

i. The organic compound (A) is 2-Ethylbenzaldehyde

ii. Its molecular formula is C₉H₁₀O.
iii. Since it is an aldehyde, it can form 2,4-DNP derivative and can reduce Tollens’ reagent. It can also undergo Cannizzaro reaction, as it does not contain α - H atom.
iv. On vigorous oxidation, both-CHO group and the ethyl side chain are oxidized to -COOH groups to give 1,2-benzene dicarboxylic acid HOOC - C₆H₄ -  COOH.