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Tautomerism

The order of ...

Question

The order of stability of the following tautomeric compounds is:
$C H_{2} = O H | C - C H_{2} - O | | C - C H_{3} ⇌ C H_{3} - O | | C - C H_{2} - O | | C - C H_{3} ⇌ C H_{3} - O H | C = C H - O | | C - C H_{3}$
$I$ $I I$ $I I I$

I > I I > I I I

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I I I > I I > I

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I I > I > I I I

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I I > I I I > I

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Solution

The correct option is B $I I I > I I > I$
The order of stability of the tautomeric compounds is $I I I > I I > I$
The tautomer III has the highest stability as the $C = C$ double bond and $C = O$ double bond are conjugated which results in delocalization and hydrogen bonding.

Tautomer I is less stable than tautomer II as the enol is less stable than keto group.
$C H_{3} - O H | C = C H - O | | C - C H_{3} > C H_{3} - O | | C - C H_{2} - O | | C - C H_{3} > C H_{2} = O H | C - C H_{2} - O | | C - C H_{3}$
$I I I$ $I I$ $I$

Option B is correct.

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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}

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I

I I

I I I

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