Why is the #C_6H_8# molecule different from benzene with respect to resonance?

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Aug 9, 2015

Answer:

Benzene has two important equivalent resonance contributors, while any other #"C"_6"H"_8# isomers have only one.

Explanation:

There are many molecules with the formula #"C"_6"H"_8#, but I suspect that you are thinking of hexa-1,3,5-triene or cyclohexa-1,3-diene

Benzene

Benzene has two equivalent resonance contributors, neither of which involves the separation of charge.

Benzene
(from chemistry.stackexchange.com)

Hexa-1,3,5-triene

Hexa-1,3,5-triene has only one important resonance contributor.

Hexatriene

(from www.chemsynthesis.com)

Any other contributor we might draw has a separation of charge. For example,

#"CH"_2"=CH-CH=CH-CH=CH"_2 ⟷ stackrel(-)("C")"H"_2"-"stackrel(+)("C")"H-CH=CH-CH=CH"_2#

Cyclohexa-1,3-diene

Cyclohexa-1,3-diene is an "almost"-benzene.

www.sigmaaldrich.com

But it is still a "linear" diene.

Like hexa-1,3,5-triene, it has only one important resonance contributor, with any other contributors having separation of charge.

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Jan 8, 2017

Benzene has 5 important resonance structures (quantum chemistry).

The idea of resonance in benzene is simple: there are two Kekule and three Dewar structures which "born" an intermediate structure between them (resonance hybrid). What is important, Kekule and Dewar structures did not exist in reality, but their overlay describes the benzene molecule.
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"enter image source here
Historic benzene formulae (from left to right) by Claus (1867), Dewar(1867), Ladenburg (1869), Armstrong (1887), Thiele (1899) and Kekulé (1865). Dewar benzene and prismane are different chemicals that have Dewar's and Ladenburg's structures. Thiele and Kekulé's structures are used today.” Benzene - Wikipedia"

One of the drawbacks of the resonance theory is that resonance structures do not exist in reality, and their objectification is a mistake. And assuming the existence of three-electron bond, we can represent the real formula of benzene, aromatic compounds, carboxylate anion, ozone, oxygen, etc. (p. 19-29 Structure of the benzene molecule on the basis of the three-electron bond. http://vixra.org/pdf/1606.0152v1...).

Here is a quote Pauling: "We can say ... that the molecule can not be satisfactorily represented by any particular structure of the valence bond and stop trying to tie its structure and properties of the structure and properties of other molecules. But, using valence bond structures as a basis for discussion, we are using the concept of resonance can give an explanation of the properties of the molecule, directly and simply in terms of other properties of the molecules. For us, convenient, for practical reasons, talk about the resonance of molecules among several electronic structures. " http://vixra.org/pdf/1607.0022v2.pdf

http://vixra.org/author/bezverkhniy_volodymyr_dmytrovych

We can represent the one true formule of benzene (p. 3 - 5): http://vixra.org/pdf/1606.0152v1...).

REVIEW. Benzene on the basis of the three-electron bond (full version, 93 p.). http://vixra.org/pdf/1612.0018v5.pdf

enter image source here
enter image source here

http://vixra.org/author/bezverkhniy_volodymyr_dmytrovych

https://www.amazon.com/Volodymyr-Bezverkhniy/e/B01I41EHHS/ref=sr_ntt_srch_lnk_1?qid=1471783006&sr=1-1

https://archive.org/details/@threeelectronbond

https://www.scribd.com/user/289277020/Bezverkhniy-Volodymyr#

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