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. What are the possible structures for the unknown compound?

(i)Empirical formula can be calculated as

Element Percentage Relative no.of atoms Simplest ratio

C 69.777 5.81 5

H 11.63 11.63 10

O 18.60 1.16 1

? Empirical formula of compound is C base 5H base 10O and empirical formula wt. = 86.

Also molecular wt. = 86.

(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