[Karakth]

The compound P C₈H₉NO gives with Zn and HCl a substance Q C₈H₁₂NCl. When sodium nitrate (III) is added to the solution of Q so obtained, an oil R separates. This, when isolated, is found to be C₈H₁₀O. When added to a solution of I₂ in water containing KOH and a little methanol, R forms a second layer which dissolves on shaking. When a slight excess of concentrated HCl is added, a white precipitate S appears C₇H₆O₂. Give structures for PQRS.

I don't know, I'm stumped... P could be an aromatic amide which goes down to amine with Zn and HCl, but as far as I know Zn and HCl are used to reduce -NO₂ groups on an aromatic ring. I suppose it could be used with the amide, but then what is the interplay of Nitrate (III) and R? Any help would be appreciated.