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

Answer 1

Answer on Question #60926 - Chemistry - Organic Chemistry

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 potassium dichromate(IV) or with warm aqueous 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

Answer:

Compound D has no hydroxyl groups to be oxidized with potassium dichromate and no unsaturated C-C bonds to react with aqueous bromine.

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