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Which carbon is most likely to form...

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sfoksn

Full Member
10+ Year Member
Sep 4, 2006
761
1
  1. Dental Student
    i think azar misunderstood the question, b/c the carbonyl carbon, as far as my limited knowledge goes, is electrophillic and is often attacked by nucleophiles.

    therefore i dont think it is a suitable candidate to form carbANION... its already lacking electrons due to oxygen right next to it...

    so can anyone give us a definite answer?
     

    RSD2014

    Full Member
    Sep 2, 2009
    202
    0
    1. Pre-Dental
      Carbanion?

      Carbonyl carbon vs. alpha carbon?

      I would think alpha carbon, but one of my problem's answer says it is the carbonyl carbon.

      Thank you.


      Alpha Carbon would be better at forming Carbanion.
      You can see it in reactions like Aldol condensation, Claisen Ester condensation and acetoacetic ester synthesis reactions. Alpha carbon is depronated to form carbanion and that attacks the Carbonyl of a second molecule to form the product. Carbonyl is usually being attacked so I assume it has a partial positive charge on the carbon. Oxygen is pulling e- away from the carbon of the carbonyl, causing it to become more positive.

      That's my understanding, feel free to correct me.
       
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