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Why is benzene stable?

benzene

benzene

Benzene has a structure that keeps on alternating between the two resonating structures. One of the cyclic structures has 1st, 3rd and 5th bonds as double bonds while the other has 2nd, 4th and 6th bonds as double bonds. The hybridization status of all the six carbon atoms is sp2 in benzene. The 2 of the sp2 orbitals of every carbon atom combine with the sp2 orbitals of the next carbon atom to create 6 different sigma bonds in the plane of the hexagon. The other remaining orbitals on every carbon atom were found to overlap with the s-orbital of the hydrogen to form C-H bonds. The p-orbitals of the carbon atoms that are free are involved in formation of pi bonds by the alternate bonds overlap.


The pi bonds are formed due to the overlap of the bonds that include C1-C2, C3-C4, C5-C6 or C2-C3, C4-C5, C6-C1. The pi bonds that are formed alternatively might get delocalized repeatedly due to their movement on the carbon atoms freely. Though there are three pi bonds, as they are delocalized frequently the benzene structure is provided with stability by these double bonds.

The electronic pi bonding and delocalization of pi electrons on both the sides of the benzene ring plane made the benzene ring to be more stable. The resonance structure imparts extra resonance energy to benzene which is found to be more stable than the other valence isomers of the benzene.

Hence, the stability of the benzene structure is provided by the p-orbitals overlap on every carbon atom in the benzene ring. The other reason is delocalization of electrons on the alternate C=C bonds. The C=C made the structure more stable thermodynamically than that was previously determined to be. The addition reaction type of the chemical reactions will have the tendency to break the delocalization in the benzene cyclic structure. Hence, benzene always prefers to participate in the substitution reactions.

Taken from: http://www.knowswhy.com/why-is-benzene-stable

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