JEE Advanced 2016 Paper 2 Chemistry: Paragraph 1

A ketone $\mathbf{P}$ (molecular formula $\mathrm{C_8H_8O}$) gives a yellow precipitate with $\mathrm{I_2}/\mathrm{NaOH}$, does not reduce Tollens' reagent, and gives ethylbenzene on Clemmensen reduction. It is converted by the following sequence. $\mathbf{P}$ reacts with $\mathrm{NH_2OH}$ to give an oxime $\mathbf{Q}$; the major isomer is the one in which the OH group is anti (trans) to the phenyl group. $\mathbf{Q}$ with $\mathrm{PCl_5}$ undergoes Beckmann rearrangement, in which the group anti to the leaving OH migrates to nitrogen, to give $\mathbf{R}$. Hydrolysis of $\mathbf{R}$ with aqueous acid under heating gives an amine $\mathbf{S}$ (isolated as its free base), which gives a foul-smelling compound with $\mathrm{CHCl_3}$/alcoholic KOH. $\mathbf{S}$ is diazotised with $\mathrm{NaNO_2}$/HCl at $0\text{-}5\ ^\circ\mathrm{C}$ to give $\mathbf{T}$, which is coupled with 2-naphthol in alkaline medium to give an intensely coloured compound $\mathbf{U}$.