Paragraph: A tertiary alcohol $H$ upon acid catalysed dehydration gives a product $I$. Ozonolysis of I leads…

Paragraph: A tertiary alcohol $H$ upon acid catalysed dehydration gives a product $I$. Ozonolysis of I leads to compounds $\mathrm{J}$ and $\mathrm{K}$. Compound $\mathrm{J}$ upon reaction with $\mathrm{KOH}$ gives benzyl alcohol and a compound $\mathrm{L}$, where $\mathrm{K}$ on reaction with $\mathrm{KOH}$ gives only $M$.
Question: The structures of compounds $J, K$ and $L$, respectively, are
  1. $\mathrm{PhCOCH}_3, \mathrm{PhCH}_2 \mathrm{COCH}_3$ and $\mathrm{PhCH}_2 \mathrm{COO}^{-} \mathrm{K}^{+}$
  2. $\mathrm{PhCHO}, \mathrm{PhCH}_2 \mathrm{CHO}$ and $\mathrm{PhCH}_2 \mathrm{COO}^{-} \mathrm{K}^{+}$
  3. $\mathrm{PhCOCH}_3, \mathrm{PhCH}_2 \mathrm{CHO}$ and $\mathrm{CH}_3 \mathrm{COO}^{-} \mathrm{K}^{+}$
  4. $\mathrm{PhCHO}, \mathrm{PhCOCH}_3$ and $\mathrm{PhCOO}^{-} \mathrm{K}^{+}$

Solution

$ J=\mathrm{PhCH}=\mathrm{O} K=\mathrm{PhCOCH}_3 \quad L=\mathrm{PhCOO}^{-} \mathrm{K}^{+} $

Asked in: JEE Advanced 2008 (Paper 2)

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