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Question -

An organic compound contains 69.77% carbon, 11.63%hydrogen and rest oxygen. 



Answer -

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.


Answer

% of carbon = 69.77 %

% of hydrogen = 11.63 %

% of oxygen = {100 − (69.77 + 11.63)}%

= 18.6 %

Thus, the ratio of the number of carbon, hydrogen, andoxygen atoms in the organic compound can be given as:

Therefore, the empirical formula of thecompound is C5H10O. Now, the empirical formula mass of the compound can begiven as:

5 × 12 + 10 ×1 + 1 × 16

= 86

Molecular mass of the compound = 86

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

Since the given compound does not reduce Tollen’s reagent,it is not an aldehyde. Again, the compound forms sodium hydrogen sulphateaddition products and gives a positive iodoform test. Since the compound is notan aldehyde, it must be a methyl ketone.

The given compound also gives a mixture of ethanoic acidand propanoic acid.

Hence, the given compound is _ Pentan-2-one.

The given reactions can be explained by the followingequations:

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