Question

Aniline reacts with mixed acid (conc. HNO₃ and conc. H₂SO₄) at 288 K to give P (51%), Q (47%) and R (2%). The major product(s) the following reaction sequence is (are) :-

$$\begin{gathered} R\underset{ 3) H O^{+} \\ 4) NaN{O}_2 , HCl/273-278K \\ 5) EtOH, ∆}{\overset{ 1)A{c}_2 O, pyridin \\ 2) B{r}_2 , CH{ }_{3}C{O}_2 H}{\to }} \end{gathered}$$$$\begin{gathered} S\underset{3) NaN{O}_2 , HCl/273-278K \\ 4) H_{3}P{O}_2}{\overset{1) Sn/HCl \\ 2) B{r}_2 /H_{2}O \left(excess\right) , }{\to }} \end{gathered}$$  major product(s)