Is Tropolone Aromatic Despite Its Unusual Structure?

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Tropolone is considered aromatic because it adheres to Hückel's rule, possessing 6 pi electrons in a cyclic, conjugated system. The discussion clarifies that the carbon atom connected to the oxygen via a double bond does indeed have a p-orbital due to the presence of a pi bond between the carbon and oxygen. This pi bond contributes to the overall aromatic character by allowing for a continuous overlap of p-orbitals throughout the ring structure. The conversation also highlights that experimental methods, such as NMR spectroscopy, can be employed to test the aromaticity of Tropolone. The participants emphasize the importance of understanding how pi bonds form and the role of p-orbitals in defining aromatic compounds.
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I understand the rules of aromaticity, but I do not understand why Tropolone is aromatic. The main reason is because I thought all the atoms in the ring have to have p-orbitals. How does the C connected the oxygen with a double bond have a p-orbital? Have to do with the resonance (that's my main guess)?

120px-Tropolone.png

It passes Hückel's rule with 6e- pi electrons and also passes other criteria.
 
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Whether a C-atom "has" a p-orbital or not is a question of definition. How would you test experimentally if Tropolone is aromatic because you are so sure about it?
 
You touched on the Hueckel rule for aromaticity but not the full definition: 4n + 2 pi electrons in a conjugated, cyclic system. Yes, this does meet that criteria.

Why do you think the carbonyl C does not have a p-orbital? There is a pi bond between C and O, so how can it not have p orbital? Can you explain more clearly what you think the problem is?
 
DrDu said:
Whether a C-atom "has" a p-orbital or not is a question of definition. How would you test experimentally if Tropolone is aromatic because you are so sure about it?

You can do NMR Spectronomy for a good result to see if it is Aromatic.

DDTea said:
Why do you think the carbonyl C does not have a p-orbital? There is a pi bond between C and O, so how can it not have p orbital? Can you explain more clearly what you think the problem is?

I understand now that C and O have a pi bond because they have a double bond between each other. I just wasn't thinking because it was late. So then there are pi bonds on all the Carbons, creating a continuous lobed structure. I was just was not thinking enough about how pi bonds form.

Thanks for your help DrDu and DDTea.
 
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