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 aditional 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

From the given elemental composition, empirical formula can be derived as:
`{:(ulbar("Element"" " C" "H" "O" ")),(ul("weight %"" "69.77" "11.63" "18.60" ")),(ul("Mole %"" "5.81" "11.63" "underset("dividing from M)")(1.1625" (obtained by"))),(ul("Simple ratio"" "5" "10" "1" ")):}`
Hence, empirical formula is `C_(5)H_(10)O` and empirical formula weight is `86`.
Since, empirical formula weight and molecular weight both are `(86)`, empirical formula is the molecular formula also.
Also, the compound does not reduce Fehling's solution therefore it is not an aldehyde, but it forms bisulphite, it must be a ketone.
Also, it gives positive iodoform test, it must be a methyl ketone.
`CH_(3)H_(7)-overset(O)overset(||)(C)-CH_(3)`
Based on the above information, the compound may be one of the following:
`underset("2-pentanone")(CH_(3)CH_(2)CH_(2)-overset(O)overset(||)(C)-CH_(3))` or `underset("3-methyl-2-butanone")(CH_(3)-overset(" "CH_(3))overset(|)(" "CH)-overset(O)overset(||)(C)-CH_(3))`