One of the many challenges that students face in the first-year organic chemistry teaching lab is understanding the connection between the synthesis and the purification of organic molecules. To facilitate the students’ comprehension of this connection, I developed an experiment that enables students to successfully carry out a single-step synthesis that requires them to divide the resulting product into three separate defined portions and to utilize one of the three independent purification techniques specific to each sample. The purification techniques investigated where liquid-liquid extraction, recrystallization, and radial chromatography. The synthesis was carried out by combining 3-nitroaniline with acetic anhydride in a Erlenmeyer flask. The resulting 3-nitroacetanilde product was collected and divided into three defined samples. Each sample was either subjected to recrystallization (from water), extraction (from ethyl acetate and 10% HCl), or radial chromatography (utilizing previously reported protocols). The purified material from each technique was massed, a percent recovery was calculated, and both a melting point and a 300 <sup>1</sup>H NMR were obtained. Based on the data that was gathered and analyzed, students hypothesized which technique provided the best acceptable yield and adequate purity of the synthesized anilide. The overall percent recoveries, physical data and spectral data analyzed where shown to be within acceptable parameters. In addition to presenting these results, this paper will also describe the methodology of this three-part independent purification of a synthesized sample of 3-nitroacetanilide.

Synthesis and the three-separate independent purification of 3-nitrooacetanilide: An exercise in recrystallization, extraction and radial chromatography in the undergraduate organic chemistry labs

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.