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Topic: sulfonation energy diagram for benzene  (Read 6330 times)

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Offline kodos

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sulfonation energy diagram for benzene
« on: December 03, 2010, 04:41:52 PM »
The next picture is an energy diagram for a typical electrophilic aromatic substitution such as nitration or bromination.

Construct a similar diagram for sulfonation.

QUESTION: I don't see the difference. The mecanism for the reaction is the same in all cases, shouldn't they have roughly the same diagram?
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Offline kodos

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Re: sulfonation energy diagram for benzene
« Reply #1 on: December 03, 2010, 05:56:05 PM »
Reuploaded the diagram:
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Offline MissPhosgene

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Re: sulfonation energy diagram for benzene
« Reply #2 on: December 03, 2010, 06:02:31 PM »
If sulfonation is done in conc. H2SO4 its reversible, but otherwise, you are right about the diagram being very similar.

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Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline kodos

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Re: sulfonation energy diagram for benzene
« Reply #3 on: December 04, 2010, 06:42:50 AM »
And reversibility means that reactants and products are on the same energy level, right? That would make a difference!
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Offline MissPhosgene

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Re: sulfonation energy diagram for benzene
« Reply #4 on: December 04, 2010, 02:56:11 PM »
Not same energy, but the energy of the ts leading from the intermediate to the product is closer in energy to the product than for example, that which occurs during bromination.
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Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.
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