Question

'A' is a neutral organic compound (M. F : $C_{8}H_{9}ON$ ). On treatment with aqueous ${Br}_{2}/{HO}^{( - )}$, 'A' forms a compound ' B ' which is soluble in dilute acid. ' B ' on treatment with aqueous ${NaNO}_{2}/HCl\left( 0 - 5^{\circ}C \right)$ 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 ${KMnO}_{4}$ produces 'F'. 'F' contains two different types of hydrogen atoms. The structure of ' A ' is