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#1 2010-05-07 15:14:29

orgopete
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Aromatic substitution of p-nitrotoluene and m-methoxybenzonitrile

Yahoo question, predict the products of bromination and chlorination of title compounds.
           http://www.curvedarrow.com/chem/ZZ10900198.jpg

The product of reaction a) will be 2-bromo-4-nitrotoluene. The location of attack is determined by the most activating substituent in substituted benzene compounds. In this case, it will be the methyl group though the nitro complements the site of reaction as it is a meta-director.

The product of reaction b) will be 3-methoxy-4-chlorobenzonitrile. The same rules apply. The methoxy is the most activating group. Because the methoxy is an o/p director, I would also expect to find some 2- and 6-chloro product as well.

It is difficult to predict the position, ortho or para for different groups. I am not aware of any definitive rules for this prediction. Some groups seem to favor ortho attack and others para.

The mechanisms for these reactions are illustrated in "A Guide to Organic Chemistry Mechanisms" (Amazon.com, Barnes and Noble or http://www.curvedarrowpress.com )

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