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  Home > JCE Print > Journal of Chemical Education > Issues > 1998  > October  >
In the Laboratory
Synthesis of Aspirin: A General Chemistry Experiment
John A. Olmsted III
Department of Chemistry and Biochemistry, California State University, Fullerton, Fullerton, CA 92834
Cover
October 1998
Vol. 75 No. 10
p. 1261
Abstract
An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer. To understand the chemistry, the student must be able to recognize the common molecular framework shared by oil of wintergreen, salicylic acid, and aspirin and to identify the -OH and -CO2 sites where chemical changes occur. The experiment differs in three ways from traditional aspirin synthesis experiments for general chemistry. It is designed to be performed early rather than late; it starts from a naturally occurring material and requires two steps rather than one; and it utilizes FTIR spectroscopy to distinguish among oil of wintergreen starting material, salicylic acid intermediate, and aspirin product. The use of FTIR spectroscopy introduces students to a modern analytical technique that is currently used in research involving aspirin.
More Information
*  Citation
 Olmsted, John A., III. J. Chem. Educ. 1998 75 1261.
*  Keywords
 introductory, high school chem, laboratory instruction
*  History
 Created:
Last Updated:		 June 21, 1999
June 24, 2005
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