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Topic: huckel's rule benzene "oxygen substituent"  (Read 3148 times)

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Offline Mikez

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huckel's rule benzene "oxygen substituent"
« on: March 13, 2011, 04:48:18 PM »
I am trying to figure out if these 2 molecules are aromatic
http://www.molport.com/buy-chemicals/directory-molecule-image/3928131/w:170/h:170

The problem is there's 2 resonance forms for the dione (2 oxygen ketones), 1 that makes it anti-aromatic and one that makes it aromatic.
*electron moves down to carbon on 1 side. moves up to oxygen on the other side
*electrons move up to oxygen
-I know that molecules are most stable as aromatic but resonance is best going to oxygen.

How do I tell which one to go with?

thanks

Offline Honclbrif

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Re: huckel's rule benzene "oxygen substituent"
« Reply #1 on: March 13, 2011, 05:54:59 PM »
If I understand what you're saying correctly, "electron moves down to carbon on 1 side. moves up to oxygen on the other side", sounds like you're moving an electron pair off of an oxygen and use it to make a bond to carbon. This would result in a carbon with 5 bonds which is usually a bad bet.
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Offline AMEDIO

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Re: huckel's rule benzene "oxygen substituent"
« Reply #2 on: March 14, 2011, 03:08:51 AM »
i doubt if the second one is aromatic??? :-\

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