The synthesis and isolation of N-tert-Butyl-2-phenylsuccinamic acid and N-tert-Butyl-3-phenylsuccinamic acid

The synthesis and isolation of the succinamic acids, 4-(tert-butylamino)-4-oxo-3-phenylbutanoic acid (3) and 4-(tert-butylamino)-4-oxo-2-phenylbutanoic acid (4), obtained by reacting phenylsuccinic anhydride (1) with tert-butylamine (2), are described. This experiment, which demonstrates that two isomeric products are obtained when an unsymmetrical anhydride is reacted with a nucleophile and that these isomers are easily separated based on their difference in acidity, is useful in introducing the topic of carboxylic acid derivatives into the organic chemistry laboratory.