An organic compound 69.77% carbon, 11.63% hydrogen and oxygen rest oxygen. The molecular mass of the compound is 86. It does not reduce Tollen's reagent but forms an addition compound with sodium hydrogensulphite and give positive indoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write the possible structure of the compound.

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Solution

Since the compound does not reduces Tollen's reagent but forms addition product.
It is ketone.
It gives idoform test, this means its a methyl ketone,
Oxidation gives ethanoic propanoic anhydride
$∴$ Total carbon=2+3=5
$∴$ possible structure

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Since the compound does not reduces Tollen's reagent but forms addition product. It is ketone.It gives idoform test, this means its a methyl ketone,Oxidation gives ethanoic propanoic anhydride ∴ Total carbon=2+3=5∴ possible structure

Since the compound does not reduces Tollen's reagent but forms addition product.
It is ketone.
It gives idoform test, this means its a methyl ketone,
Oxidation gives ethanoic propanoic anhydride
$∴$ Total carbon=2+3=5
$∴$ possible structure