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Oxidation of Pyruvate

An aromatic c...

Question

An aromatic compound 'A' (Molecular formula $C_{8} H_{8} O$ ) gives positive $2, 4$ -DNP test. It gives a yellow precipitate of compound ' $B$ ' on treatment with iodine and sodium hydroxide solution. Compound ' $A$ ' does not give Tollen's or Fehling's test. On drastic oxidation with potassium permanganate it forms a carboxylic acid ' $C$ ' (Molecular formula $C_{7} H_{6} O_{2}$ ), which is also formed along with the yellow compound in the above reaction. Identify $A$ , $B$ and $C$ and write all the reactions involved.

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Solution

Benzoic acid
$C_{8} H_{8} O$
$D . U = \frac{8 (4 - 2) + 8 (1 - 2) + 1 (2 - 2)}{2} + 1$
$= \frac{16 - 8}{2} + 1$
D.U. = $\frac{8}{2} + 1$
= 5

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