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Topic: Friedel Crafts Alkylation  (Read 4637 times)

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Offline Joules23

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Friedel Crafts Alkylation
« on: July 17, 2008, 02:03:38 PM »


I thought this reaction will not occur because FC-alkylation cannot work with an EWG as the substituent?

Offline macman104

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Re: Friedel Crafts Alkylation
« Reply #1 on: July 17, 2008, 02:07:01 PM »
You don't *just* have an EWG though.  You also have a EDG from the cycloalkane, yes?

EDG direct to which positions?  Which position is the Cl in relative to the cycloalkane?
EWG direct to which positions?  Which position is the Cl in relative to the nitro group?

Can you see the reinforcement that forces the Cl into the position it's in?

Offline Joules23

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Re: Friedel Crafts Alkylation
« Reply #2 on: July 17, 2008, 02:21:23 PM »
Thanks!!

Offline spirochete

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Re: Friedel Crafts Alkylation
« Reply #3 on: July 17, 2008, 09:44:05 PM »
Also that is a halogenation, not a FC-alkylation.  Maybe the OP confused them because they both use strong lewis acid catalysts?

Offline macman104

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Re: Friedel Crafts Alkylation
« Reply #4 on: July 17, 2008, 11:17:22 PM »
Good catch!  Very possibly that is why.  For the electrophilic aromatic substitution, I agree they may just see AlCl3 and think FC.

Offline Joules23

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Re: Friedel Crafts Alkylation
« Reply #5 on: July 19, 2008, 11:34:23 AM »
ahhh OK.. so even if the cycloakane wasnt there, and the only substituent was NO2, the reaction will still occur because it is halogenation?

Offline spirochete

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Re: Friedel Crafts Alkylation
« Reply #6 on: July 19, 2008, 03:06:09 PM »
correct

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