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Fundamental Concepts in Organic Reaction Mechanism - Hyperconjugation

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Maharashtra State Board: Class 12

Definition: Hyperconjugation

The stabilising interaction that involves delocalisation of σ-electrons of C–H bond of an alkyl group linked directly to an atom of unsaturated system or to an atom having unshared p-orbital, is called hyperconjugation.

e.g.

Maharashtra State Board: Class 12

Key Points: Hyperconjugation

Also called the Baker-Nathan effect or no-bond resonance.

Conditions for hyperconjugation:

  • The compound must have at least one sp²-hybridised carbon (alkene, alkyl carbocation, or alkyl free radical)
  • The α-carbon must have at least one H–C bond attached to the unsaturated system
  • More the number of H–C bonds at α-carbon → greater the stabilisation → more stable the alkene/carbocation

Resonance vs. Hyperconjugation:

Feature Resonance Hyperconjugation
Electrons involved π electrons delocalised σ electrons of C–H bond delocalised
Stability provided Greater Lesser
Bond type π bond σ bond
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