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Resonance

Which of the ...

Question

Which of the following compounds have higher enol content than keto content?

A

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B

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C

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D

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Solution

The correct options are
B
D

Due to the presence of $H -$ bond, these compounds have maximum enol content. Also, compound D in enol form is aromatic.

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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.
Which one of the following compounds has maximum enol content?

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