Discussion
An organic compound with molecular formula,C5H10O, does not reduce Tollen's reagent but forms an addition compound with sodium hydrogen sulphite and gives positive iodoform test. On vigorous oxidation, it gives ethanoic and propanoic acids. The compound is
Answer: C
The compound is pentan-2-one.
Each clue narrows it down. C5H10O with no Tollens' reaction is a ketone, not an aldehyde, so pentanal is out. Forming a bisulphite adduct and giving the iodoform test both point to a methyl ketone, CH3CO-R.
Pentan-2-one, CH3COCH2CH2CH3, fits, and vigorous oxidation cleaves it beside the carbonyl to give ethanoic acid and propanoic acid.
Pentan-3-one has no CH3CO group and fails the iodoform test. Ethoxyethane and pentanol are not carbonyl compounds (and ethoxyethane is C4H10O).
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