Q.

'A' is a neutral organic compound (M.F.: C8H9ON). On treatment with aqueous Br2/HO(-), 'A' forms a compound 'B' which is soluble in dilute acid. 'B' on treatment with aqueous NaNO2/HCl (0-5°C) produces a compound 'C' which on treatment with CuCN/NaCN produces 'D'. Hydrolysis of 'D' produces 'E' which is also obtainable from the hydrolysis of 'A'. 'E' on treatment with acidified KMnO4 produces 'F'.  'F' contains two different types of hydrogen atoms.  The structure of 'A' is       [2026]

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Ans.

(3)