[confusedstud]

Can we say that one requirement of drawing resonance structures where we push electrons around is that all the atoms participating have to be sp2 hybridized (including radicals since carbons with radicals are also sp2 hybridized)?

And the electrons that we push around must be from the unhybridized p orbital?

If so, can electrons move in sp hybridized orbitals for example: https://imgur.com/UoaP0OU

In the two cases in the image, the electrons are pushed from and to unhybridized p orbitals. So why can't they happen?

I was thinking about this for a while, and for the top structure its not possible because from the left to right structure delocalization and hybridization has to occur? And for the bottom structure, for that to happen the electron has to delocalize into the p orbital that is perpendicular to the p orbitals which is also impossible?