Chlorobenzene has been sulfonated homogeneously in aqueous sulfuric acid varying from 83.4 to 99.6 wt‐%, at 25°. The isomer distribution‐98.8% para, 0.8% ortho, 0.4% meta ‐ is constant over the acid range studied. The substrate isotope effect has been determined under conditions of rapid hydrogen exchange; kD/kH varies from 0.8 in 95% sulfuric acid to 0.4 in 97%. The dependence of the reaction rate and the isotope effect on the acid concentration is explained by an SE2‐mechanism involving attack by H2S2O7 followed by proton removal from the σ‐complex by HSO4−; the latter process is partly rate‐limiting at high acid concentrations.
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Kort et al. (1967) studied this question.
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