November 27, 2024, 06:27:24 PM
Forum Rules: Read This Before Posting


Topic: Acidity of aldehyde (and other carbonyls)  (Read 912 times)

0 Members and 1 Guest are viewing this topic.

Offline supinemagpie

  • Very New Member
  • *
  • Posts: 1
  • Mole Snacks: +0/-0
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

  • Chemist
  • Full Member
  • *
  • Posts: 892
  • Mole Snacks: +97/-24
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.

Sponsored Links