Why is benzene extraordinarily stable though it contains three double bonds?


Benzene is the hybrid of the resonating structures shown below:-


Now, all the six carbon atoms in benzene are sp2 hybridized. The two sp2 hybrid orbitals of each carbon atom overlap effectively with the sp2 hybrid orbitals of adjacent carbon atoms to form six sigma bonds in the hexagonal plane. The remaining sp2 hybrid orbital on each carbon atom overlaps with the s-orbital of hydrogen to form six sigma C–H bonds. The remaining unhybridized p-orbital of carbon atoms has the possibility of forming three π bonds by the lateral overlap of –


C1 & C2;


C3 & C4;


C5 & C6;





C2& C3;


C4 & C5;


C6 & C1;





The six π orbitals and their electrons are delocalized and hence can move freely about the six carbon nuclei. Even after the presence of the three double bonds, these delocalized π-electrons stabilize benzene.


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