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In the Laboratory
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Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-Bromobenzoate
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Eric J. Mahan and Mary Alice Nading
Department of Chemistry, University of Hartford, West Hartford, CT 06117
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November 2006
Vol. 83 No. 11
p. 1652
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| Abstract |
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This experiment was designed to help students improve the critical thinking skills that are required to analyze and discuss the results of an organic chemistry experiment in an effective manner. The initial objective indicated in the prelab handout for this puzzle experiment was the synthesis of methyl 4-bromobenzoate using the Fischer esterification. Before beginning the experiment, however, students were informed that someone, acting as a "mole", might have sabotaged their experiment so that different results would be obtained. Their new objective was to perform the experiment, determine if any sabotage had occurred, and, if so, identify the changes that were made to the reagents as well as the person who was responsible for these modifications. Using the results from the experiment, spectroscopic data for the reagents provided by the instructor, and melting point values from chemical reference materials, students were able to complete this goal and become more adept at analyzing the outcome of a synthetic organic chemistry experiment. The Fischer esterification is found in many laboratory manuals and the series of carboxylic acids used for this procedure are safe and relatively inexpensive, so the experiment should be adaptable to most organic laboratory curricula.
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| Supplement |
Instructions for the students and notes for the instructor are available .
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| More Information |
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Citation |
Mahan, Eric J.; Nading, Mary Alice. J. Chem. Educ. 2006 83 1652.
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Keywords |
Alcohols; Carboxylic Acids; Esters; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; Mass Spectrometry; NMR Spectroscopy; Organic Chemistry; Problem Solving / Decision Making; Second-Year Undergraduate; Synthesis
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History |
Created:
Last Updated: |
9/19/2006
9/20/2006
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 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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