Question:
An organic compound with the molecular formula C9H10O forms 2, 4-DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1, 2-benzenedicarboxylic acid. Identify the compound.
Solution:
It is given that the compound (with 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 given reactions can be explained by the following equations.
