Reaction of iso-propylbenzene with $\mathrm{O}_2$ followed by the treatment with $\mathrm{H}_3…

Reaction of iso-propylbenzene with $\mathrm{O}_2$ followed by the treatment with $\mathrm{H}_3 \mathrm{O}^{+}$forms phenol and a by-product $\mathbf{P}$. Reaction of $\mathbf{P}$ with 3 equivalents of $\mathrm{Cl}_2$ gives compound $\mathbf{Q}$. Treatment of $\mathbf{Q}$ with $\mathrm{Ca}(\mathrm{OH})_2$ produces compound $\mathbf{R}$ and calcium salt $\mathbf{S}$. The correct statement(s) regarding $\mathbf{P}, \mathbf{Q}, \mathbf{R}$ and $\mathbf{S}$ is(are)
  1. Reaction of $\mathbf{P}$ with $\mathbf{R}$ in the presence of $\mathrm{KOH}$ followed by acidification gives
  2. Reaction of $\mathbf{R}$ with $\mathrm{O}_2$ in the presence of light gives phosgene gas
  3. $\mathbf{Q}$ reacts with aqueous $\mathrm{NaOH}$ to produce $\mathrm{Cl}_3 \mathrm{CCH}_2 \mathrm{OH}$ and $\mathrm{Cl}_3 \mathrm{CCOONa}$
  4. $\mathbf{S}$ on heating gives $\mathbf{P}$

Solution

(1) (2) $\underset{(\mathrm{R})}{\mathrm{CHCl}_3} \xrightarrow{\mathrm{O}_2} \underset{\text { Phosgene gas }}{\mathrm{COCl}_2}+\mathrm{HCl}$ (3) $Q$ does not undergo Cannizaro reaction (4)

Asked in: JEE Advanced 2024 (Paper 1)

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