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Greg E.
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Dissenter
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I am told by Dr. Klein that in the nitration of benzene, hydrogen sulfate anion acts as the base and deprotonates the sigma complex.

enter image description here

My question is why would the hydrogen sulfate anion be doing the deprotonation? We've just established that sulfuric acid is a stronger acid than nitric acid; hence sulfuric acid is able to protonate nitric acid to some extent. Now are we expected to believe that the conjugate base of a stronger acid is stronger than the conjugate base of a weaker acid? Why not have nitrate anion do the deprotonation? It is a stronger base after all than hydrogen sulfate anion.

I am told by Dr. Klein that in the nitration of benzene, hydrogen sulfate anion acts as the base and deprotonates the sigma complex.

enter image description here

My question is why would the hydrogen sulfate anion be doing the deprotonation? We've just established that sulfuric acid is a stronger acid than nitric acid; hence sulfuric acid is able to protonate nitric acid to some extent. Now are we expected to believe that the conjugate base of a stronger acid is stronger than the conjugate base of a weaker acid? Why not have nitrate anion do the deprotonation? It is a stronger base after all than hydrogen sulfate anion.

I am told by Dr. Klein that in the nitration of benzene, hydrogen sulfate anion acts as the base and deprotonates the sigma complex.

enter image description here

My question is why would the hydrogen sulfate anion be doing the deprotonation? We've just established that sulfuric acid is a stronger acid than nitric acid; hence sulfuric acid is able to protonate nitric acid to some extent. Now are we expected to believe that the conjugate base of a stronger acid is stronger than the conjugate base of a weaker acid? Why not have nitrate anion do the deprotonation? It is a stronger base than hydrogen sulfate anion.

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Dissenter
Dissenter
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Nitration of Aromatic Compounds

I am told by Dr. Klein that in the nitration of benzene, hydrogen sulfate anion acts as the base and deprotonates the sigma complex.

enter image description here

My question is why would the hydrogen sulfate anion be doing the deprotonation? We've just established that sulfuric acid is a stronger acid than nitric acid; hence sulfuric acid is able to protonate nitric acid to some extent. Now are we expected to believe that the conjugate base of a stronger acid is stronger than the conjugate base of a weaker acid? Why not have nitrate anion do the deprotonation? It is a stronger base after all than hydrogen sulfate anion.