Deduce the structural formula of a compound, $C_{10} H_{10} (A)$ that gives $(B)$ on oxidation:

$H O O C (B) - C H_{2} - C | C H_{2} - C O O H H - C H_{2} - C O O H$

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Solution

Degree of unsaturation $= \frac{2 n_{1} - n_{2} + 2}{2} = \frac{20 - 10 + 2}{2} = 6$
Thus, there may be $6 π$ bonds. Presence of three carboxylic acids confirm that there are three triple bonds in $^{'} A^{'}$ .
$(A) \to H C \equiv C - C H_{2} - C | C H_{2} - C \equiv C - H H - C H_{2} - C \equiv C - H$ .

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