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Jun19-09, 08:37 PM
P: 5
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.
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