Question

An unknown compound of carbon, hydrogen and oxygen contains $69.77\%$ carbon and $11.63\%$ hydrogen and has a molecular weight of $86$. It does not reduce Fehling solution, but forms a bisulphite addition compound and gives a positive iodoform test. How many possible structures can be drawn for the unknown compound?

Answer 1

Answer: 2

Empirical formula can be calculated as

$\therefore$ Empirical formula of compound is $C_5{H}_{10}O$ and empirical formula wt. $=86$. Also molecular wt. $=86$ $\therefore$ Molecular formula of compound is $C_5{H}_{10}O$.
(ii) Compound forms bisulphite addition compound and thus has carbonyl gp, i.e. aldehyde or ketone.
(iii) It does not reduce Fehling solution and thus it is not an aldehyde but a ketone.
(iv) It gives positive iodoform test and thus it has unit,