What is hyperconjugation?

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What is hyperconjugation?

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Answer 1 · 2017-07-22T00:39:03

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

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

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

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

$3^{\circ} > 2^{\circ} > 1^{\circ} > methyl$ $3^@ > 2^@ > 1^@ > "methyl"$ $carbocation$ $"carbocation"$ ,

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

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What is hyperconjugation?

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