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Tautomerism

Which of the ...

Question

Which of the following has the highest percentage of enol form in Keto-enol equilibrium?

A

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B

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C

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D

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Solution

The correct option is C
The enol form of 2, 4-Hexanedione is more stable due to the resonance stability of conjugated double bond and also due to the formation of cyclic six membered ring by hydrogen bonding.
Other enol forms of (a), (b) and (d) lack this stabilisation.

Hence, (c) has the highest percentage of enol in Keto-enol equilibrium.

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Similar questions

Q. Which of the following has the highest percentage of enol form in Keto-enol equilibrium?

In which one of the following keto-enol system is the keto form more stable than the enol form?

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Q. The conversion of a keto form into enol is enolisation. It depends on structural factor, temperature and nature of solvent. Resonance and hydrogen bonding increases enol content. Enolic form of phenol is more stable than keto form by -13 kcal/mole of energy hence phenol exist exclusively as an enol. Enolic tautomer is less polar due to intramolecular hydrogen bonds than the corresponding keto form.Any polar solvent would decrease the enolisation and favour keto form intramolecular hydrogen bonding stablized enol form by 7kcal/mole and resonance stabilizes enol form by 15 kcal/mole.
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