Both the lone pairs on the oxygen are in allylic positions, thus both should be able to participate in resonance. If both lone pairs can participate in resonance, why is only one of the lone pairs delocalized?

Also, for a lone pair to participate resonance, does it have to be in an unhybridized p orbital? If so that would explain why only one of the lone pairs is delocalized as one of the lone pairs would be in an unhybridized p orbital to make it sp2 for oxygen.

  • 2
    $\begingroup$ Yes, your last statement is exactly why. The p-orbital on the oxygen overlaps with the p-orbitals on the carbons, the sp2 electron pair does not. $\endgroup$ – ringo May 10 '19 at 3:15

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