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Sulfonation of Benzene
Reaction type: Electrophilic Aromatic Substitution
Summary
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Step 1: The p electrons of the aromatic C=C act as a nucleophile, attacking the electrophilic S, pushing charge out onto an electronegative O atom. This destroys the aromaticity giving the cyclohexadienyl cation intermediate. |
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Step 2: Loss of the proton from the sp3 C bearing the sulfonyl- group reforms the C=C and the aromatic system. |
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Step 3: Protonation of the conjugate base of the sulfonic acid by sulfuric acid produces the sulfonic acid.
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© Dr. Ian Hunt, Department of Chemistry |