Organic Compound Synthesis Pathway

‘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