Electrophilic aromatic subsitution reactions on polysubstituted benzenes are governed by the same rules we learned for mono-substituted benzenes.
This is the simplest case when both groups are the same. There's only one possibility since all four sites are equivalent.
In some cases, the directing effects reinforce one another. For example, the CH3 (ortho/para-director), reinforces that of the -NO2 (meta-director).
If there is a difference between the activating ability of the two groups then regiochemistry is controlled by the more powerful activating group. In this case the -OH group is a more powerful ortho/para director than the -CH3.
At what position would an EAS reaction occur in the following molecule?
Login