November 29, 2024, 03:43:13 AM
Forum Rules: Read This Before Posting


Topic: Protonating oxygen on a carbonyl  (Read 2338 times)

0 Members and 1 Guest are viewing this topic.

Offline Woopy

  • Regular Member
  • ***
  • Posts: 85
  • Mole Snacks: +4/-8
Protonating oxygen on a carbonyl
« on: April 08, 2013, 09:07:53 PM »
Hello,

I was wondering, why does protonating the oxygen on a carbonyl compound increase the electrophilicity of the carbonyl carbon? Wouldn't it be pushing electron density toward the carbon, since the oxygen is not pulling the density away as much since it is positively charged?

Offline discodermolide

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
Re: Protonating oxygen on a carbonyl
« Reply #1 on: April 08, 2013, 09:28:06 PM »
Well I think that oxygen does not really like to carry a positive charge. So putting one on a carbonyl oxygen by protonation will cause the electrons to drift towards the oxygen to try and compensate for the charge, this results in the carbon atom becoming more positive, i.e. a better electrophile.
Very simplistic explanation. Perhaps someone can be more scientific?
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline Dan

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 4716
  • Mole Snacks: +469/-72
  • Gender: Male
  • Organic Chemist
    • My research
Re: Protonating oxygen on a carbonyl
« Reply #2 on: April 09, 2013, 03:26:04 AM »
Wouldn't it be pushing electron density toward the carbon, since the oxygen is not pulling the density away as much since it is positively charged?

I don't understand your logic. If something is positively charged, what does it attract?
My research: Google Scholar and Researchgate

Sponsored Links