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:
| Reaction Temperature | |
Isomer of the Product | 0 °C | 100 °C |
o-toluenesulfonic acid | 43% | 13% |
m-toluenesulfonic acid | 4% | 8% |
p-toluenesulfonic acid | 53% | 79% |
(a) Explain the change in the product ratios when the temperature is increased.
(b) Predict what will happen when the product mixture from the reaction at 0°C is heated to 100°C.
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