Alcohols and Ethers - Result Question 33

Passage 1

A tertiary alcohol $H$ upon acid catalysed dehydration gives a product $I$. Ozonolysis of $I$ leads to compounds $J$ and $K$.

Compound $J$ upon reaction with KOH gives benzyl alcohol and a compound $L$, whereas $K$ on reaction with KOH gives only $M$.

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$(2008,3 \times 4 M=12 M)$

36. The structures of compounds $J, K$ and $L$ respectively, are

(a) $PhCOCH _3, PhCH _2 COCH _3$ and $PhCH _2 COO^{-} K^{+}$

(b) $PhCHO, PhCH _2 CHO$ and $PhCOO^{-} K^{+}$

(c) $PhCOCH _3, PhCH _2 CHO$ and $CH _3 COO^{-} K^{+}$

(d) $PhCHO, PhCOCH _3$ and $PhCOO^{-} K^{+}$

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Answer:

Correct Answer: 36. (d)

Solution:

Passage 1

Compound $J$ must be benzaldehyde because it on treatment with KOH undergoing Cannizzaro’s reaction producing benzyl alcohol and pot-benzoate ( $L$ ).

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