Question 9.3: Predict the major product of the sulfonation of toluene.

Predicting the Product of an Electrophilic Aromatic Substitution Reaction

Predict the major product of the sulfonation of toluene.

S t r a t e g y
Identify the substituent present on the ring, and decide whether it is ortho- and para-directing or meta-directing. According to Figure 9.18, an alkyl substituent is ortho- and para-directing, so sulfonation of toluene will give primarily a mixture of o-toluenesulfonic acid and p-toluenesulfonic acid.