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Electrophilic nature of Carbon in CO2

  1. May 10, 2014 #1

    Qube

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    How is the carbon in carbon dioxide electrophilic? There is no partial positive charge on the carbon in carbon dioxide because the molecule is symmetrical.
     
  2. jcsd
  3. May 10, 2014 #2

    AGNuke

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    You can consider one of the pi bond in C-O bond to jump to O, thus leaving C with electron deficit, thus making it electrophile.

    If you are talking about how it takes part as electrophile in various organic addition reaction, this is the way it works.
     
  4. May 10, 2014 #3

    Qube

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    I think I got it; the carbon in carbon dioxide is electrophilic because the oxidation state of the carbon in that molecule is +4. I think what you described is what happens when carbon acts as an electrophile; I was just looking for why and I didn't see that using formal and partial charges - formal charge analysis says the carbon is neutral; partial charge analysis says that the carbon bears no partial charge because the dipoles formed by the oxygens cancel out, but oxidation state analysis tells me that the electrons bide their time with the oxygens instead of the carbon. Thank you :).
     
  5. May 10, 2014 #4

    Borek

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    I don't understand the argument. Linear molecule O=C=O having partial positive charge on the carbon and half negative charges on oxygens is quite symmetrical.
     
  6. May 10, 2014 #5

    Qube

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    Oops, I can see it now. So even if the dipoles cancel out, there can be partial charges?
     
  7. May 10, 2014 #6

    AGNuke

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    Partial charges are seen in terms of individual bond. Since C=O bond is polar, you are expected to see partial charges.
     
  8. May 10, 2014 #7

    Qube

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    Ah, good distinction. Thank you :)!
     
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