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.
Solution
The given molecular formula C9H10O forms 2,4 –DNP derivative and reduces tollen’s reagent. Therefore, the given compound must be an aldehyde. Again the compound undergoes cannizzaro reaction and on oxidation gives 1,2 –benzenedicarboxylic acid. Therefore, the –CHO group is directly attached to a benzene ring and this benzaldehyde is ortho-substituted. Hence, the compound is 2-ethylbenzaldehyde.
The above mechanism is given as,
