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

Step 1. To find out the molecular formula of the compound.
`%C=69.77%,%H=11.63%`
`therefore%O=100-(69.77+11.63)=18.6%`
`C:H:O=(69.77)/(12):(11.63)/(1)=(18.6)/(16)=5.88:11.63:1.16=5:10:1`
`therefore`The E.F. of the given compound is `C_(5)H_(10)O`
E.F. mass`=5xx12+12xx1+1xx16=86`
Since, mol. mass=86 (Given)
`thereforeM.F.=C_(5)H_(10)Oxx(86)/(86)=C_(5)H_(10)O`
Step 2. To determine the structure of the compound
(i) Since the givenc ompound forms sodium hydrogen sulphite addition product, therefore, it must be either an aldehyde or methyl ketone.
(ii) Since the compound does not reduce tollens' reagent, therefore, it cannot e an aldehyde and hence it must be a methyl ketone.
(iii) Since the given compound on vigorous oxidation gives a mixture of ethanoic acid and propanoic
Acid, therefore, the methyl ketone is pentan-2-one, i.e., `underset("Pentan-2- one ")(M.F.C_(6)H_(10)O)(CH_(3)-overset(O)overset(||)(C)-CH_(2)CH_(2)CH_(3))`
Step 3. To explain the reactions involved in the given questions.
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