periodicity
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So i'm doing a question which asks out of pyrrole and pentadiene which is more acidic.
I know that pentadiene becomes aromatic on deprotonation, but I am unsure about pyrrole.
I think the N atom will be sp2 hybridised but I am not sure whether that means there can be resonance of the negative charge or not.
I want to say that pyrrole would be stronger due to the better electronegativity of N/lower energy sp2 orbital but again I'm not sure if pyrrole has no resonance if that would be better than the aromatic cyclopentadiene.

So basically: is resonance possible in the pyrrole conjugate base, if yes/no, why/why not? And then which one is stronger and why?

Second question:
Acidity of the attached two compounds - I want to say electronegativity of O atom is greater therefore more stabilised conjugate base for pyridone, but apparently this is wrong.

Thanks for your help!
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