In the reference link below, the chemical synthesis of sulfanilamide from acetanilide is shown in schematic form. Sulfanilamide is basically a benzene ring core with a primary amine (NH2) on one side and a sulfonamide group (SO2NH2) on the other side. The synthesis is a three step process where the final step is the hydrolysis of an acetamide group (NHCOCH3) to the primary amine (NH2). Basically the compound is treated with either a strong aqueous acid or strong aqueous base to perform the hydrolysis. But there are two groups that are potentially hydrolyzable in the molecule. The group most readily hydrolyzable is the acetamide group as previously mentioned. But the sulfonamide group is also potentially hydrolyzable if the reaction is carried on for too long. If the sulfonamide group were to hydrolyze, then the final product would have a sulfonic acid group (SO3H) instead.
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