Question:

Why is benzene extra ordinarily stable though it contains three double bonds?

Updated On: Nov 15, 2023
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Solution and Explanation

Benzene is a hybrid of resonating structures given as:

hybrid of resonating structures

All six carbon atoms in benzene are sp2 hybridized. The two sp2 hybrid orbitals of each carbon atom overlap 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 unhybridizedp-orbital of carbon atoms has the possibility of forming three π bonds by the lateral overlap of \(C_1-C_2,\ C_3-C_4,\ C_5-C_6\  \text {or}\  C_4-C_5,\ C_6-C_1\).

Structured representation of benzene

The six \(\pi's\) are delocalized and can move freely about the six carbon nuclei. Even after the presence of three double bonds, these delocalized \(\pi\)-electrons stabilize benzene.

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Concepts Used:

Aromatic hydrocarbon

Aromatic hydrocarbons, sometimes known as arenes, are aromatic organic molecules made up entirely of carbon and hydrogen. In aromatic compounds a benzene ring which is named after the simple aromatic chemical benzene, or a phenyl group when part of a larger structure, is the configuration of six carbon atoms.

Read More: Aromaticity

Reactions of Aromatic Hydrocarbons:

1. Aromatic Substitution Reactions

This reaction involves the replacement of one substituent on the ring of an aromatic hydrocarbon, commonly a hydrogen atom, by a different substituent group.

The common types of aromatic substitution reactions are:

  • Nucleophilic aromatic substitution reactions
  • Electrophilic aromatic substitution reactions
  • Radical nucleophilic aromatic substitution reactions

2. Coupling Reactions

In these types of reactions, the coupling of two fragments that have a radical nature is achieved with the help of a metal catalyst