Many esters have characteristic odors. Methyl salicylate exhibits a pleasant wintergreen odor. This ester can be prepared from salicylic acid and methanol via Fischer esterification. Which one of these reagents would you use in excess in order to drive the reaction to the product? Explain how you would isolate the ester product from the reaction mixture for full credit. (10 pts)

Methanol would be used as a reagent in excess, since it is a very low-cost solvent. For product isolation, the first thing to do is remove the methanol through a distillation process. The residue produced can be dissolved in diethyl ether. Using a NaHCO₃ solution, extraction is performed. When it separates into two phases, the product will be in the ether and the reagent in the aqueous phase. The ether can also be removed by distillation, and at the end of this process you will have the product you want.

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