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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > March  >
In the Laboratory
Synthesis and Characterization of 9-Hydroxyphenalenone Using 2D NMR Techniques
Benjamin Caes and Dell Jensen, Jr.
Department of Chemistry, Augustana College, Rock Island, IL 61201-2296
Cover
March 2008
Vol. 85 No. 3
p. 413

Abstract
9-Hydroxyphenalenone is a planar multicyclic β-keto–enol, which is synthesized via a Friedel–Crafts acylation followed by acid-catalyzed intramolecular Michael addition with the loss of a phenyl group in a one-pot reaction during a four-hour lab period. Tautomerization of the β-keto–enol results in C symmetry on the NMR time scale, which simplifies the spectra and provides a unique structure for teaching 2D NMR spectroscopy. The 1H and 13C assignments can be made using 1D and 2D NMR techniques and data collection can be reduced to less than twenty minutes with optimized parameters.
Supplement
Details of the synthesis; NMR parameters; Processing lists; Student spectra
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Citation
Caes, Benjamin; Jensen, Dell, Jr. J. Chem. Educ. 2008, 85, 413.
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Keywords
Alcohols; Aldehydes / Ketones; Aromatic Compounds; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Problem Solving / Decision Making; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
2/4/2008
2/8/2008
 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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