Why Are Some Resonance Structures Less Common?

AI Thread Summary
Resonance structures vary in stability based on the electronegativity of atoms and formal charge distribution. In the discussed molecule, the structure with a negatively charged oxygen and a positively charged carbon is favored due to oxygen's higher electronegativity, which aligns with the tendency of electronegative atoms to hold negative charges. Other proposed structures, such as those with a carbanion on carbon or positive charge on oxygen, are less favorable because they violate the typical charge distribution rules. The preference for certain resonance forms is rooted in their stability and the overall energy of the molecule. Understanding these principles helps clarify why some resonance structures are less common.
nobahar
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Hello!

I have silly question on resonance, it's so silly, I couldn't find an answer:
Lets say there is a O=CR-CH=CH2 bonding in a molecule, R = some other group. You can get (I have put the charges in brackets and Superposition (I think that's what its called):
(1-)O-C=C-C(1+) (ignoring hydrogens for simplicity)
But why not (1+)O-C=C-C(1-)? Why not the carbanion, and the oxygen with the positive charge?
And if the 2 electrons from the pi-bond can transfer on to the oxygenm, why not nay of the other carbons, e.g. (1+)O-C(1-)-C=C and O=C-C(1-)-C(1+)?
Does that make sense? Is it because they are just so unfavourable they are not worth including?

Any help appreciated!
Thankyou!
 
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I'm not an expert, but this is how I see it:
in the (-1)O-C=C-C(1+), O is more electronegative than C, so it would have a higher tendency to gain electrons. Also, if you look at formal charges, negative charges are usually associated with more electronegative atoms and positive charges with less electronegative. I think if you apply this reasoning of formal charges to the other structures you've shown, (-1)O-C=C-C(1+) ends up being the most reasonable one.
 
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