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Topic: Benzene addition  (Read 4172 times)

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Offline AlIXe

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Benzene addition
« on: November 13, 2007, 03:30:27 PM »
Hi

From what I understand Benzene cannot easily undergo addtion because it is reluctant to "break up" it's stable delocalised structure. This is what all the books say. However I require a little more detail. Why will it not easily undergo addition?

Is it because you would have to overcome the delocalisation energy of 150kjmol-1? What is the delocalisation energy exactly? Is it the energy the 6 delocalised electrons possess??

Help is desperately needed

Thank you

Offline AlIXe

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Re: Benzene addition
« Reply #1 on: November 14, 2007, 04:35:54 PM »
Hi

Any help please - anyone?

Offline ARGOS++

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Re: Benzene addition
« Reply #2 on: November 14, 2007, 05:09:48 PM »

Dear AlIXe;

Would you really like to talk about Addition and not about Substitution?
Remember by Addition the result will not be anymore of aromatic character! You will have destroyed it.

For Stabilisation Energy you may start with reading:   "Resonance Energy
(Search for “Hydrogenation” therein, –  that’s a real Addition.)

I hope it may help you, at least for the start.

Good Luck!
                   ARGOS++

Offline AWK

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Re: Benzene addition
« Reply #3 on: November 15, 2007, 01:39:09 AM »
Benzene also undergoes addition, but with a different radical mechanism, eg
C6H6 + 3Cl2 = C6H6Cl6

se also
Benzene as Dienophile in the Diels-Alder Reaction
Angewandte Chemie International Edition in English
Volume 14, Issue 3, Date: March 1975, Pages: 181-182
Wolfgang Jarre, Dieter Bieniek, Friedhelm Korte
AWK

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