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Topic: Acidity of aldehyde (and other carbonyls)  (Read 654 times)

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Offline supinemagpie

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Acidity of aldehyde (and other carbonyls)
« on: March 29, 2020, 11:42:23 AM »
Say you have a molecule like aldehyde:
O=C
Is it valid to think about a resonance form where the pi electrons in the double bond go completely to the oxygen, leaving the carbon a carbocation and forming a zwitterion. I know this would be a highly unfavored resonance structure, but would the fact that this resonance structure exists contribute to increased the acidity of the carbon in aldehyde?

Offline pgk

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Re: Acidity of aldehyde (and other carbonyls)
« Reply #1 on: March 30, 2020, 10:30:35 AM »
Please, do not confuse electrophilicity/ nucleophilicity with acidity/ basicity. Otherwise, serious misunderstoods may arise.
Indicatively, Pearson’s HSAB theory mainly refers to electrophilicity/ nucleophilicity and not to “pure” acidity/ basicity.
Besides, Brønsted-Lowry refers to chemical compounds as chemical entities and not to their resonance structures.

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