1. Tardigrade
  2. Question
  3. Chemistry
  4. 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?

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Q. 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?

Aldehydes Ketones and Carboxylic Acids

Solution:

Empirical formula can be calculated as
image
$\therefore \quad$ Empirical formula of compound is $C _{5} H _{10} O$ and empirical formula wt. $=86$. Also molecular wt. $=86$ $\therefore \quad$ 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,
image