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Desulfonation of benzenesulfonic acid

Moose1942  Follow
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I never have seen this HSO3+. Existing do HSO3-

Benzene sulfonic acid is very stable in water, also the second reaction wouldn't take place.

At high T sulfonation is reversible

Bruckner, Reinhard - Organic Mechanisms Reactions Stereochemist

As I understand it, in diluted H2SO4 there should be no hydrogen in the sulfonic groups. And also how would it proceed if we deal with sodium benzene sulfonate?

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Bengt Nyman  Follow
I never have seen this HSO3+. Existing do HSO3-

Benzene sulfonic acid is very stable in water, also the second reaction wouldn't take place.

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David Beckham  Follow
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Here you have an naphthalen system with some more substituents, in some circumstance as here shown this reaction takes place in concentrated sulfuric acid.

Fine. Let's assume that this is naphthalene sulfonic acid in diluted sulfuric acid and sodium salt of this acid (just have not got a reference at hand, but in some textbooks they give example of desulfonation using bezene sulfonic acid; it does not matter much).

The acid is deprotonated (or there is an anion in solution in case of salt). What is the mechanism of desulfonation?

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Antonio Moroni  Follow
Here you have an naphthalen system with some more substituents, in some circumstance as here shown this reaction takes place in concentrated sulfuric acid.

In Benzene sulfonic acid  not much will happen.

see synthesis of it : http://en.wikipedia.org/wiki/Benzenesulfonic_acid

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