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?

C H_{3} C O C H_{2} C O O C H_{3}

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C H_{3} C O C H_{2} C O O C_{2} H_{5}

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C H_{3} C O C H_{2} C O C H_{3}

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C_{6} H_{5} C O C H_{2} C O C_{6} H_{5}

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Solution

The correct option is D $C_{6} H_{5} C O C H_{2} C O C_{6} H_{5}$
$C_{6} H_{5} - O | | C - C H_{2} (d - c) - O | | C - C_{6} H_{5}$
$d - c$ is between 2 Ewc group so more acidic and hence d-H is easily available for 1, 3 shift.
So it shows Tautomerism and with max. exeel content.
d-H can be easily moved to either sides on $- O | | C -$ group.

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Similar questions

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

In keto - enol tautomerism of dicarbonyl compounds, the enol form is preferred in contrast to the keto-form this is due to

[C H_{3} C O C H_{3}]

< 0.1 %

[C H_{3} C O C H_{2} O C C H_{3}]

15 %

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