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Question

List the limitations of Kekule's structure ?


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Solution

Kekule structure:

  • Kekule's structure was the first suggested structure for Benzene.
  • In this structure, the Carbons are arranged in a hexagon manner, and it has been suggested that there exist alternating double and single bonds between them.
  • In this, each Carbon atom has a Hydrogen attached to it, which can be shown in the figure as:
Illustrated Glossary of Organic Chemistry - Kekulé structure

The list of the Limitations of Kekule's structure:

  • According to the prediction made by the Kekule structure, there should be two different 1,2-bromobenzene, which represent the two different bonds present in the benzene structure.
  • But in actual practice, only one 1,2-bromobenzene has ever been found, denoting the fact that all the bonds in benzene are equivalent and form resonance with each other.
  • According to Kekule's structure benzene contains three double bonds and hence the chemical properties of benzene should resemble those of alkene, but in actuality, it is not so as Benzene is highly stable and forms substitution compounds easily.
  • Kekule structure predicted that there are two types of bond lengths that exist in the structure i.e the bond length for the single bonds 1.54Aand for double bonds 1.34A, but actually all the bonds of benzene are found to be of equal length.

Hence, above are the mentioned list of the Limitations of Kekule's structure.


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