1. Reactions of Carboxylic Acids, Carboxylate Salts, and Carboxylate Esters Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University

2. Reactions Flow Chart Classify the reactant. Carboxylic Acid Reaction Conditions? Carboxylic Acid + base “Acid-Base Reaction” Remove the hydrogen from the carboxyl group and bond it to the “O” or the “N” of the base to form water or an ammonium ion, respectively. Pair the cation with the carboxylate ion. Carboxylic Acid + Alcohol + H2SO4 “Esterification” Remove the OH from the carboxyl group and the H from the O of the alcohol to form H2O. Form a bond between the O of the alcohol and the C of the carboxyl group to form an ester. Carboxylate Salt with an acid Break the bond between the H and the acid and bond H to the carboxylate group to form a carboxylic acid. Carboxylate Ester Reaction Conditions? Carboxylate Ester + H2O + NaOH “Saponification” Break the C-O of the carboxylate group. Break the H-O of the water. Bond the H to the O-R to form an alcohol. Bond the OH from the water to the C of the carboxylate group. Then remove the hydrogen from the carboxyl group and bond it to the “O” of t he base to form water. Pair the cation with the carboxylate ion. Carboxylate Ester + H2O + acid “Acid Catalyzed Hydrolysis” Break the C-O of the carboxylate group. Break the H-O of the water. Bond the H to the O-R to form an alcohol. Bond the OH from the water to the C of the carboxylate group.

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