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Home » Question 12.19: 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 addition compound with sodium hydrogensulphite and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write the possible structure of the compound.
Question 12.19: 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 addition compound with sodium hydrogensulphite and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write the possible structure of the compound.
Aldehydes, Ketones, and Carboxylic Acids | CBSE | Chemistry | Class 12 | Guides | NCERT
Question 12.19: 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 addition compound with sodium hydrogensulphite and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write the possible structure of the compound.

Solution:

The number of carbon, hydrogen, and oxygen atoms in an organic compound can thus be expressed as:

Therefore, the empirical formula of the compound is C5H10O. Now, the empirical formula mass of the compound can be given as:

Molecular mass of the compound = 86

Therefore, the molecular formula of the compound is given by C5H10O.

Because the provided compound does not reduce Tollen’s reagent, it is not an aldehyde. The substance produces sodium hydrogen sulphate addition products as well as a positive iodoform test. It must be a methyl ketone because the chemical isn’t an aldehyde.

A mixture of ethanoic acid and propanoic acid is also produced by the given chemical.

Hence, the given compound is pentan−2−ol.

The reactions can be illustrated by the following equations:

i

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