Unlike most other electrophilic aromatic substitutions, sulfonation is often reversible (see Section 17-4). When one sample of toluene is sulfonated at 0 °C and another sample is sulfonated at 100 °C, the following ratios of substitution products result:
(c) Because the SO3H group can be added to a benzene ring and removed later, it is sometimes called a blocking group.
Show how 2,6-dibromotoluene can be made from toluene using sulfonation and desulfonation as intermediate steps in the synthesis.
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Master EAS Review with a bite sized video explanation from Johnny Betancourt