Question

A certain industrial cleaner and paint solvent was distilled to produce a single compound D. When D reacted with 2,4-dinitrophenylhydrazine, an orange precipitate was produced. With alkaline aqueous iodine, D gave a pale yellow precipitate. D did not react either with warm acidified pottasium dichromate(IV) or with warm aqueos bromine. Reduction of D with hydrogen over a catalyst produced an equimolecular mixture of two isomers, E and F with molecular C4H10O.
Suggest structural formulae of D,F and E and explained the reaction involved