Creatine Synthesis: An Undergraduate Organic Chemistry Laboratory Experiment

Andri L. Smith and Paula Tan
Department of Chemistry, Quinnipiac University, Hamden, CT 06518
J. Chem. Educ., 2006, 83 (11), p 1654
DOI: 10.1021/ed083p1654
Publication Date (Web): November 1, 2006

Abstract

Students in introductory chemistry classes typically appreciate seeing the connection between course content and the "real world". For this reason, we have developed a synthesis of creatine monohydrate—a popular supplement used in sports requiring short bursts of energy—for introductory organic chemistry laboratory courses. Creatine monohydrate is easily synthesized from N-methylglycine (sarcosine) and cyanamide in the presence of salt and base. The crude product is purified by recrystallization and analyzed by thin-layer chromatography, melting point, and nuclear magnetic resonance spectroscopy. This synthesis illustrates the electrophilic nature of nitriles, as well as the nucleophilic nature of amines.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Amines / Ammonium Compounds

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History

  • Received: August 03, 2009

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