Radicalic Bromination with Norbornane as instructive example -Insights in Basic Organic Chemistry 45
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- เผยแพร่เมื่อ 6 ก.พ. 2025
- The old rule that tertiary CH groups react the fastest does not apply to bicyclic norbornane. We are clarifying the reasons.
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You comment that part of the reason the tert-butyl radical is stabilized is due to the elongation of the C-C bonds due to rehybridization from sp3 to sp2. However, isn't the sp2 orbital smaller than the sp3 orbital? I expected those bonds to shorten. I am thinking about bond lengths in stable molecules and you are talking about radicals. How is it different professor?
I`ve watched that video once again, and did not find anything about elongation of CC-Bonds. The three methyl-groups increase the distance from each other because of change in bond angles. And additionally the CC-bonds become shorter due to partial double bond character. Then, don?t forget that knowone has ever seen a sp3 or an sp2 orbital, these are mathematical models (having a lo t of benefits in explaining the findings. In addition, because of recent experimental results, one has to modify the model fpor the Norbornane system a little bit:
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