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Topic: meso compounds  (Read 4651 times)

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Offline smilegirl

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meso compounds
« on: May 18, 2008, 08:00:21 PM »
Does a benzene ring have resonance structures even if it is highly substituted?
Thanks

Offline spirochete

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Re: meso compounds
« Reply #1 on: May 18, 2008, 11:57:36 PM »
When you draw resonance structures for benzene which orbitals are the electrons delocalized into?  What type of orbitals are they?  What type of oribital would be used to make bonds to substituents? 

Offline smilegirl

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Re: meso compounds
« Reply #2 on: May 19, 2008, 12:04:01 PM »
the orbitals are sp2, so there would be one sigma and one pi bond

Offline spirochete

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Re: meso compounds
« Reply #3 on: May 19, 2008, 04:08:21 PM »
That's correct each carbon is SP2 hybridized, although this means it makes 3 sigma bonds with its sp2 hybrid orbitals and a Pi bond with its P orbital.  But you still need to think about which oribtals are involved in resonance to understand the answer to your question.

If you want you can also make a model of benzene to see the orientation of the orbitals.  The P orbital in each atom is perpindicular to the plane of the sigma bonding oribitals.

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