Sulfonylation of Arenes to give sulfonic acids

by James

Description: Treatment of an aromatic molecule such as benzene with sulfur trioxide and a strong acid leads to formation of sulfonic acids.
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{ 7 comments… read them below or add one }

T.R.Prajapati April 29, 2012 at 9:56 am

i want to prepare sulfonic acid at small scale industry.pl give us details.

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james April 29, 2012 at 1:00 pm

You should hire a consultant.

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Polina Porotsky February 12, 2015 at 4:52 pm

Does sulfonation activate the ring for future electrophilic aromatic substitutions?

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James February 12, 2015 at 4:56 pm

No, SO3H is an electron withdrawing group so it actually deactivates the ring. Hope this helps! James

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Polina Porotsky February 13, 2015 at 6:09 pm

Wonderful. Thank you. Electron withdrawing due to the electronegative oxygens, and the fact that the Pi orbitals are not the same size? Would it be useful as an instigator for addition-elimination nucleophilic aromatic substitution? (the same way that NO2 is?)

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Taylore Bonn March 15, 2015 at 2:50 am

Why does benzene pie attack the S? It already has 6 bonds?

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James March 17, 2015 at 10:57 pm

It’s not easy to do – but it happens. It’s much more difficult to perform this reaction on benzene than on an ordinary alkene. It’s usually important to heat this reaction.

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