What is the hybridization if it has resonance?

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If you had an amide, the hybridization for the nitrogen would be sp^3 because it has two bonded Hydrogens, a bond to the carbonyl carbon, and a lone pair.
However, if you drew the resonance structure, the N would be sp^2

So do you say that the nitrogen is sp^2 or sp^3? Based on what I've seen in the BR book, it assumes the smallest hybridization, so sp^2. But in my EK1001 orgo practice, it looks like it would be sp^3.

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If you had an amide, the hybridization for the nitrogen would be sp^3 because it has two bonded Hydrogens, a bond to the carbonyl carbon, and a lone pair.
However, if you drew the resonance structure, the N would be sp^2

So do you say that the nitrogen is sp^2 or sp^3? Based on what I've seen in the BR book, it assumes the smallest hybridization, so sp^2. But in my EK1001 orgo practice, it looks like it would be sp^3.
From what I understood is that you would always assume the smallest hybridization you can. Like the oxygen in the amide: normally (with no charge) it has sp2. But with a negative formal charge, it has sp3. When thinking about the hybrid of a molecule, the electron is literally going from the nitrogen to the oxygen back to N back to O etc. Its so delocalized that the molecule assumes the smallest hybridization in order to account for an incoming electron charge.
 
You should understand that resonance forms are not distinct forms of compound - the compound exists in all of these resonance forms at once (a superposition, if you will) and so if a lone pair can delocalize, it is delocalized. So it will be sp2. This is why something like aniline is not very basic.
 
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