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A tertiary alcohol (H) upon acid-catalys...

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).

Compound (H) is formed by the reaction of:

A

B

C

D

Text Solution

Verified by Experts

The correct Answer is:
B

i. Reaction of (J) with KOH suggests that it is Cannizzaro reaction. Therefore, (L) must be `PhCOOK` and (J) is `(PhCHO)`.
ii. Structure of (M) is given, and it is `alpha-beta`-unsaturated ketone. It suggests that(M) is obtained by the Aldol condensation of (K). So proceed reverse to get the structure of (K).

iii. Again proceed reverse to get the structure of (I) and (H).

Reaction of (J):
`underset((J))(PhCHO) + underset((J))(PhCHO) overset(KOH)rarr underset((L))(PhCOOK) + PhCH_(2)OH`
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Knowledge Check

  • 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). The structurer of compound (I) is:

    A
    B
    C
    D

  • 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). 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 `PhCH_(2)COO^(-)K^(+)`
    C
    `PhCOCH_(3), PhCH_(2)CHO`, and `CH_(3)COO^(-)K^(+)`
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    `PhCHO, PhCOCH_(3)`, and `PhCOO^(-)K^(+)`

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