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Question

Which will be the least stable resonating structure:

A
CH2=CHCHCHOCH3
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B
CH2CHCH=CHOCH3
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C
CH2CH=CHCH=OCH3
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D
CH2=CHCHCH=OCH3
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Solution

The correct option is D CH2=CHCHCHOCH3
The three factors responsible for carbocation stability are-
1. More the number of alkyl groups attached to carbocation more is stability.
2. More the number of multiple bonds more will be charge delocalization and more is carbocation stability.
3. Neighbouring atoms with lone pairs.
The form A is least stable as the electron-rich carbon with a negative charge is adjacent to highly electronegative oxygen causing high electron density which destabilizes the carbocation and least stable.

Hence, the correct option is A

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