Refer to the order of stability among carboxylic acid derivatives to predict the ease of carrying out a given acyl transfer reaction. Among common derivatives, the acyl chloride form is the most unstable, followed in order by acid anhydride, ester, amide, and lastly carboxylate (or carboxylic acid), the most stable (lowest free energy). Reaction equilibrium favors the more stable form. For this reason it is a simple process to carry out the saponification of an ester by a strong base and transform the relatively unstable ester molecule into a carboxylate anion. The most common use of this reaction is the saponification of triglyceride to make soap.
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