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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > July  >
In the Laboratory
The Preparation and Enzymatic Hydrolysis of a Library of Esters
Elizabeth M. Sanford and Traci L. Smith
Department of Chemistry, Hope College, Holland, MI 49422-9000
Cover
July 2008
Vol. 85 No. 7
p. 944

Abstract
An investigative case study involving the preparation of a library of esters using Fischer esterification and alcoholysis of acid chlorides and their subsequent enzymatic hydrolysis by pig liver esterase and orange peel esterase is described. Students work collaboratively to prepare and characterize the library of esters and complete and evaluate the feasibility of the enzymatic hydrolysis for the goals of the case. Students make extensive use of 1H NMR to characterize products and to determine the product or products of the enzymatic reaction. The interdisciplinary nature of this experiment in the context of a case study allows students to make connections to biology; see how chemical and biological approaches to a problem differ and complement each other; gain experience in a sequential three-step synthesis and the characterization of mixtures; and develop group skills and reflective judgment.
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Detailed student instructions and materials, instructor notes, experimental and survey results, and lists of chemicals and their hazards
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Citation
Sanford, Elizabeth M.; Smith, Traci L. J. Chem. Educ. 2008, 85, 944.
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Keywords
Collaborative / Cooperative Learning; Drugs / Pharmaceuticals; Enzymes; Esters; Hands-On Learning / Manipulatives; Industrial Chemistry; Inquiry-Based / Discovery Learning; Interdisciplinary / Multidisciplinary; IR Spectroscopy; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Synthesis; Thin Layer Chromatography
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History
Created:
Last Updated:
5/27/2008
6/4/2008
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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