What is hyperconjugation?

1 Answer
Jul 22, 2017

Hyperconjugation is an extended delocalization of electron density from a sigma bond into an adjacent, non-full p nonbonding or pi orbital that stabilizes the resultant compound.


A common instance of this occurs in organic chemistry on carbocations.

Adjacent alkyl groups contain "C"-"H" sigma bonds that will interact with the central empty p nonbonding orbital in the carbocation to stabilize the electropositive carbon by providing negative charge density:

http://www.chem.ucalgary.ca/

Thus, the more alkyl groups around the carbocation (e.g. the more substituted the carbocation), the more stable it is, i.e.

3^@ > 2^@ > 1^@ > "methyl" "carbocation",

the tertiary carbocation is more stable than the secondary, which is more stable than the primary, which is more stable than the methyl carbocation.