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  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > September  >
In the Laboratory
A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions
A. Gilbert Cook
Department of Chemistry, Valparaiso University, Valparaiso, IN 46383
Cover
September 2007
Vol. 84 No. 9
p. 1477

Abstract
An experiment is presented that has the student execute a Knoevenagel initiated annulation reaction. The reaction can be carried out either through use of a microwave reactor or by allowing the mixture to stand at room temperature for two days. The student is then challenged to identify the reaction product through a guided prelab exercise of the synthesis of the Hagemann ester, and then through GC–MS, NMR, and IR spectra of the product. The stereochemistry of the product is determined through the NMR spectrum and the Karplus curve. The student is required to write a mechanism for the reaction.
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Instructions for the students, notes for the instructor, and GC, NMR, and IR spectra are available.
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Citation
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
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Keywords
Aldehydes / Ketones; Conformational Analysis; Gas Chromatography; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; IR Spectroscopy; Laboratory Instruction; Mass Spectrometry; Mechanisms of Reactions; NMR Spectroscopy; Organic Chemistry; Problem Solving / Decision Making; Second-Year Undergraduate; Stereochemistry; Synthesis; Upper-Division Undergraduate
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History
Created:
Last Updated:
7/23/2007
8/16/2007
 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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