Question

Orgo II Tutorial: Esterification and Ester Reactions

Answer 1

\({\bf{Synthetic~Methods:}}\)
1. Fisher esterification: uses carboxylic acid + an alcohol (or phenol). must be acid-catalyzed

Answer 2

2. react acyl chloride or carboxylic anhydride w/ alcohol (see tutorial on carboxylic acid anhydrides)

3. trans-esterification: high-boiling ester with high-boiling alcohol to create higher boiling ester and low boiling alcohol and separate through distillation. must be acid-catalyzed

Answer 3

\({\bf{Hydrolysis:}}\)

1. Saponification (base-catalyzed) ester reacts with NaOH and water to replace the OR group on the ester with an O-Na+ , forming the carboxylate and alcohol



2. Acid-catalyzed; ester reacts with water and replaces the OR with an OH, creating an alcohol in the process

Answer 4

Anyway, that's the end of my tutorial, I hope it was a helpful resource. Source material is Organic Chemistry 12th edition by Solomons, et. al.