'A' is a neutral organic compound (M. F : $\mathrm{C}_8 \mathrm{H}_9 \mathrm{ON}$ ). On treatment with aqueous $\mathrm{Br}_2 / \mathrm{HO}^{(-)}$, ' A ' forms a compound ' B ' which is soluble in dilute acid. ' B ' on treatment with aqueous $\mathrm{NaNO}_2 / \mathrm{HCl}\left(0-5^{\circ} \mathrm{C}\right)$ produces a compound ' C ' which on treatment with $\mathrm{CuCN} / \mathrm{NaCN}$ produces ' D '. Hydrolysis of ' D ' produces ' E ' which is also obtainable from the hydrolysis of ' A '. ' E ' on treatment with acidified $\mathrm{KMnO}_4$ produces ' F '. ' F ' contains two different types of hydrogen atoms. The structure of ' A ' is

The formal charges on the atoms marked as (1) to (4) in the Lewis representation of $\mathrm{HNO}_3$ molecule respectively are

Sodium fusion extract of an organic compound $(\mathrm{Y})$ with $\mathrm{CHCl}_3$ and chlorine water gives violet color to the $\mathrm{CHCl}_3$ layer. 0.15 g of $(\mathrm{Y})$ gave 0.12 g of the silver halide precipitate in Carius method. Percentage of halogen in the compound $(\mathrm{Y})$ is

$\_\_\_\_$ . (Nearest integer)

(Given : molar mass $\mathrm{g} \mathrm{mol}^{-1} \mathrm{C}: 12, \mathrm{H}: 1, \mathrm{Cl}: 35.5, \mathrm{Br}: 80, \mathrm{I}: 127$ )

The cycloalkene $(\mathrm{X})$ on bromination consumes one mole of bromine per mole of $(\mathrm{X})$ and gives the product $(\mathrm{Y})$ in which $\mathrm{C}: \mathrm{Br}$ ratio is 3:1. The percentage of bromine in the product $(\mathrm{Y})$ is $\_\_\_\_$ %. (Nearest integer)

(Given : molar mass in $\mathrm{g} \mathrm{mol}^{-1} \mathrm{H}: 1, \mathrm{C}: 12, \mathrm{O}: 16, \mathrm{Br}: 80$ )