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Carbon-Carbon Bond Energies: Primary vs. Tertiary Carbon

  1. Jun 19, 2009 #1
    Hi, first time poster.

    Quick question:

    Why is the bond energy for a bond that contains a more highly substituted (tertiary) carbon weaker than the bond energy of a bond that contains a less substituted (primary) carbon?

    Let me clarify with an example. Say Bond A is a single bond between a methyl carbon and a carbon that has a double bond. Another bond (Bond B) also has a single bond but between a tertiary carbon and another carbon that has a double bond. So, both share an sp2-hybridized and an sp3-hybridized carbon. Now, I know that Bond B has a weaker bond energy because it contains the more highly substituted carbon, but I don't know why that is the case. I figured that the carbons pull some of the electron density away from Bond B, therefore, lengthening the bond and decreasing the bond energy. Is that correct?

    Much thanks!

    Edit: Hmmm. Now that I think about it, I don't know if this question should be posted on this board. Sorry about that.
     
    Last edited: Jun 19, 2009
  2. jcsd
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