‘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) produ

Question

‘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

(A) C N CH3 H O
(B) NH2 CH3 O
(C) NH2 O CH3
(D) CONH2 CH3

Prashant Kotian · Accepted Answer

Correct answer: C. CH3 C–NH2 O KOH Br2 CH3 NH2 NaNO2 HCl CH3 N2Cl CuCN CH3 CN HOH H CH3 COOH HOH / H + – ALLEN  CH3 COOH KMnO4 COOH COOH

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