Stability of Conjugated Dienes

Conjugated dienes are more stable than non conjugated dienes (both isolated and cumulated) due to factors such as delocalization of charge through resonance and hybridization energy. This can also explain why allylic radicals are much more stable than secondary or even tertiary carbocations. This is all due to the positioning of the pi orbitals and ability for overlap to occur to strengthen the single bond between the two double bonds.

The resonance structure shown below gives a good understanding of how the charge is delocalized across the four carbons in this conjugated diene. This delocalization of charges stablizes the conjugated diene:

Along with resonance, hybridization energy effect the stability of the compound. For example in 1,3-butadiene the carbons with the single bond are sp2 hybridized unlike in nonconjugated dienes where the carbons with single bonds are sp3 hybridized. This difference in hybridization shows that the conjugated dienes have more 's' character and draw in more of the pi electrons, thus making the single bond stronger and shorter than an ordinary alkane C-C bond (1.54Å).