How does Hyperconjugation stabilize a Carbon Free Radical? [closed]








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I tried drawing the resonance structures but just cannot see how *donating two electrons to a carbon that **only needs one electron*** make it more stable?


I stumbled upon [this question](https://chemistry.stackexchange.com/questions/91449/does-hyperconjugation-stabilize-a-carbocation-more-than-a-free-radical) asked years ago where they say that hyperconjugation stabilizes the carbocation, but does not stabilize free radical that much.


I cannot seem to find a solid reasoning for it other than a Free Radical requires electron from an electron donating group. Note that I am just just highschooler knowing learning about intermediates for the first time. Any help would be much appreciated!




Hyperconjugation means that the $\sigma$-bond orbital interacts with an adjacent empty anit-bonding orbital. This means that the interaction between a filled orbital and an empty orbital is the factor that stabilizes the carbocation in this case. However in the case of a carbon radical, there would be at least one electron in the anti-bonding (or non-bonding) orbital, which would be destabilizing the interaction. Just to clarify on the point why Hyperconjugation cannot stabilize a Carbon Free radical as much as a carbocation, the repulsion between the electrons would be larger in the case of a carbon free radical, than in the case of a carbocation.



> 
> I tried drawing the resonance structures but just cannot see how donating two electrons to a carbon that only needs one electron make it more stable?
> 
> 
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[![enter image description here](https://i.stack.imgur.com/2PF8p.png)](https://i.stack.imgur.com/2PF8p.png)


As you said only 1 electron is needed,actually only 1 electron is donated as you can see in hyperconjugation structures above.


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