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Topic: Limitation of Friedel Crafts reaction  (Read 4471 times)

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Offline Dolphinsiu

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Limitation of Friedel Crafts reaction
« on: May 03, 2007, 03:25:50 PM »
Why nitro- / sulphonic acid substituted benzene will form complex with and deactivate AlCl3 catalyst?

The book just say the condition just like FC acylation.

CH3COCl + AlCl3 ---> CH3C(+)OAl(-)Cl4

But I don't know why? Can only can know the complex-forming mechanism in case of nitro- / sulphonic acid substituted benzene ?

Thank you!
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Offline Dolphinsiu

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Re: Limitation of Friedel Crafts reaction
« Reply #1 on: May 04, 2007, 03:48:16 AM »
O.. It seems no one know why and how they form complex with AlCl3.

But I only know NH2 gp can form complex

NH2   ---- >  H2N+---Al-Cl3
 l                     l
Ph                  Ph
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Offline PRIYA1022

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Re: Limitation of Friedel Crafts reaction
« Reply #2 on: May 04, 2007, 12:20:37 PM »
OK....Now do you think nitrobenzene or benzene-sulphonic acid can form a complex with AlCl3( A LEWIS ACID)?
and if you know the directing  nature of nitro/and HSO3 groups on a benzene ring( I assume you  learned this in your school) , do you think you can get a "strong electrophile" from  Friedal Crafts condition?
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Offline Dolphinsiu

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Re: Limitation of Friedel Crafts reaction
« Reply #3 on: May 05, 2007, 02:42:07 AM »
Actually I don't think they will form complex, but I only know nitro/sulphonic acid group will act as meta-directing group
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