Among the following, the compounds having the highest enol content is:

C H_{3} C H O

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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 H O

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C H_{3} - C O - C H_{2} - C O_{2} C H_{3}

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Solution

The correct option is C $C H_{3} - C | | O - C H_{2} C H O$
Among the following, the compound having the highest enol content is present in $C H_{3} - C | | O - C H_{2} C H O$ .
Ketonic form predominates in simple monocarbonyl compounds like acetone, acetophenone and acetic acid. This is due to greater strength of $C = O$ present in keto form than C=C bond present in enol form. Enolic form predominates in 1,3 dicarbonyl compounds such as $C H_{3} - C | | O - C H_{2} C H O$ .

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I_{2} / N a O H

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

I I

I I I

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}

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

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

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