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Topic: Friedel-Crafts Alkylation  (Read 1967 times)

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Offline confusedcollegestudent

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Friedel-Crafts Alkylation
« on: July 29, 2017, 08:14:33 PM »
My professor said that if there is already a meta director or a strong EDG, there won't be a reaction.
She gave us an example, m-phthalic acid, which she says does not undergo any reaction if it reacts with CH3Cl and AlCl3
However, there was a problem, p-nitrobenzoic acid undergoing a chlorination even though it has two EDG like the m-phthalic acid does.
Why is this? Is this because the two groups are different on the nitrobenzoic acid and the phthalic acid aren't?

Offline kriggy

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Re: Friedel-Crafts Alkylation
« Reply #1 on: July 30, 2017, 04:18:36 AM »
The difference is that one reaction is FC alkylation and the other is halogenation. You cant compare those two directly.
Also, I dont realy see a reasong why strong EDG would stop the FC alkylation when the reaction is SEAr which gets promoted by electron donating groups, didnt she mean EWG? It seems you have the terms confused: EDG = electron donating group (increases electron density on the aromatic ring), EWG= electron withdrawing group (decreases electron density on the aromatic ring)

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