Hyperconjugative effect
(1) When a H-C bond is attached to an unsaturated system such as double bond or a benzene ring, the sigma ( σ ) electrons of the H-C bond interact or enter into conjugation with the unsaturated molecules. The communication between the electrons of systems (multiple bonds) and the adjacent σ bonds (single H-C bonds) of the substituent groups in organic compounds is called hyperconjugation. The principle of hyperconjugation was prepared by Baker and Nathan and is also known as Baker and Nathan effect.
In fact hyperconjugation effect is similar to resonance effect. Since there is no interaction between the -carbon molecule and one of the hydrogen molecules, the hyperconjugation is also known as no-bond resonance.
(2) Structural needs for hyperconjugation
(i) Compound could have at least one Sp2-hybrid carbon of either alkene alkyl carbocation or alkyl free radical.
(ii) -carbon with respect to Sp2 hybrid carbon should have at least one hydrogen.
If both these conditions are fulfilled then hyperconjugation will take place in the molecule.
(iii) Hyperconjugation is of three kinds
(iv) Resonating structures because of hyperconjugation may be written involving "no bond" between the alpha carbon and hydrogen atoms.
(v) Number of resonating structures due to the hyperconjugation = Number of -hydrogens + 1.
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