Why Are Some Resonance Structures Less Common?

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SUMMARY

The discussion centers on the stability of resonance structures in organic molecules, specifically the bonding configuration O=CR-CH=CH2. The participant highlights the resonance forms (1-)O-C=C-C(1+) and (1+)O-C=C-C(1-), questioning the absence of the carbanion structure. The conclusion drawn is that the electronegativity of oxygen makes it more favorable to hold a negative charge, while carbon tends to stabilize positive charges. This reasoning aligns with the principles of formal charge distribution in resonance structures.

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  • Understanding of resonance structures in organic chemistry
  • Knowledge of electronegativity and its impact on charge distribution
  • Familiarity with formal charge calculations
  • Basic concepts of molecular bonding and hybridization
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  • Study the principles of resonance and stability in organic molecules
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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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