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  Home > JCE Print > Journal of Chemical Education > Issues > 1995  > August  >
Laboratory Experiments
Structure Determination Using 19-F NMR: A Simple Fluorination Experiment of Cinnamyl Alcohol
Daniel J. deMendonca, Cheryl A. Digits, Erin W. Navin, Tanya C. Sander, and Gerald B. Hammond
University of Massachusetts Dartmouth, North Dartmouth, MA 02747
Cover
August 1995
Vol. 72 No. 8
p. 736
Abstract
Described here is the nucleophilic substitution of a hydroxyl group, in cinnamyl alcohol, by fluorine, and analysis of the product using 19-F NMR spectroscopy. This experiment brings important innovations to the teaching of experimental organic chemistry at the undergraduate level. The fluorination of cinnamyl alcohol requires only a mild fluorinating agent and so it provides the student with a direct contact with organofluorine, chemistry. The allylic nucleophilic substitution typified by our experiment will enhance the instruction of nucleophilic substitution in the laboratory, traditionally limited to SN1 or SN2 substitutions. Because the ratio of SN2 to SN2' derived products cannot be determined directly using 1-H NMR spectroscopy but it can be measured easily using 19-F NMR spectroscopy. The experiment gives the student a firsthand experience of the usefulness of NMR spectra of different nuclei.
More Information
*  Citation
 deMendonca, Daniel J.; Digits, Cheryl A.; Navin, Erin W.; Sander, Tanya C.; Hammond, Gerald B. J. Chem. Educ. 1995 72 736.
*  Keywords
*  History
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Last Updated:		 10/1/1999
5/22/2006
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