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

Explanation

`C=69.77%,H=11.67%`
`therefore" "O=100-(69.77+11.63)%=18.6%`
`therefore" "C:H:O=(69.77)/(12):(11.63)/(1):(18.6)/(16)=5.88:11.63:1.16::5:10:1`
The empirical formula of the given compound `=C_(5)H_(10)O`
Empirical formula mass `=5xx12+10xx1+1xx16=86`
Molar mass = 86 (given)
`therefore` Molecular formula `=C_(5)H_(10)O`
Since the compound form sodium hydrogen sulphite addition product, therefore, it must be either an - aldehyde or methyl/cyclic ketone. Since the compound does not reduce. Tollens' reagent therefore, it cannot be an aldehyde. Since the compound gives positive iodoform test, therefore, the given compound is a methyl ketone Since the given compound on vigorous oxidation gives a mixture of ethanoic acid and propanoic acid therefore, the methyle ketone is pentan-2-one, i.e.,