An organic compound
′X′ forms an orange-yellow precipitate with
2,4−DNP reagent. It does not react with aqueous
[Ag(NH3)2]NO3.X on reduction with
NaBH4 gives a secondary alcohol and on oxidation with nitric acid yields a dicarboxylic acid containing the same number of carbon atoms. On bromination,
X gives a monobromo product. On the basis of these reactions, it can be concluded that
X:
I. contains aldehydic carbonyl group.
II. contains ketonic carbonyl group
III. contains ester carbonyl group
IV. does not contain C=C bonds.