Which of the following has maximum enol content :

C H_{3} - C ∥ O - H

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C H_{3} - C ∥ 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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Solution

The correct option is D $C H_{3} - C ∥ O - C H_{2} - C ∥ O - C H_{3}$
$C H_{3} C O C H_{2} C O C H_{3}$ has maximum enol content.
Due to intramolecular H-bonding and resonance stabilization enol content is maximum.

Hence, option D is correct.

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C H_{2} = O H | C - C H_{2} - O | | C - C H_{3} ⇌ C H_{3} - O | | C - C H_{2} - O | | C - C H_{3} ⇌ C H_{3} - O H | C = C H - O | | C - C H_{3}

I

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C H_{2} = O H | C - C H_{2} (I) - O | | C - C H_{3} ⇌ C H_{3} - O | | C - C H_{2} (I I) - O | | C - C H_{3}

⇌ C H_{3} - O H | C = C H (I I I) - O | | C - C H_{3}

{C H}_{3} - {C H}_{2} - O ∥ C - {C H}_{2} - {C H}_{2} - {C H}_{3}

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C H_{3} - C | | O - C H_{3} I C H_{3} - C | | O - C | | O - C H_{3} I I C H_{3} - C | | O - C H_{2} - C | | O - C H_{3} I I I

C H_{3} - C H_{3} | C = O

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