Textbook Problem

. Salicylic acid is an interesting molecule: it is both an acid and an alcohol, having a hydroxyl group attached to the aromatic ring (phenol). For this reason, salicylic acid can undergo two different etherification reactions depending on which functional group of salicylic acid reacts. For example, as discussed in this chapter, when treated with acetic acid—a stronger acid—salicylic acid behaves as an alcohol, and the ester produced is acetylsalicylic acid (aspirin). On the other hand, when reacted with methyl alcohol, salicylic acid behaves as an acid, and the ester methyl salicylate (oil of wintergreen) is produced. Methyl salicylate is also an analgesic and is part of the formulation of many liniments for sore muscles. Write an equation for the production of each of these esters of salicylic acid.