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  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > March  >
In the Laboratory
Isolating trans-Anethole from Anise Seeds and Elucidating Its Structure: A Project Utilizing One- and Two-Dimensional NMR Spectrometry
Joseph W. LeFevre
Chemistry Department, State University of New York at Oswega, NY 13126
Cover
March 2000
Vol. 77 No. 3
p. 361
Abstract
This three-week project involves isolating and purifying a natural product and determining its structure. trans-Anethole is isolated from anise seeds by steam distillation and liquid-liquid extraction. The crude product is analyzed by thin-layer chromatography and purified by flash chromatography. A variety of one- and two-dimensional NMR methods, along with infrared spectroscopy, are used to elucidate the structure. The one-dimensional NMR methods are proton homonuclear decoupling, Distortionless Enhancement by Polarization Transfer (DEPT), and Nuclear Overhauser Effect (NOE) difference spectroscopy. The two-dimensional NMR methods are proton-proton COrrelated SpectroscopY (COSY) and HETeronuclear CORrelated spectroscopy (HETCOR). Finally, the proton and carbon-13 NMR spectra are assigned.
Supplement
The following is included as supplementary material: a detailed student handout, which includes explanations and examples of the NMR techniques; and Instructor's Notes, which contain the 1H and 13C NMR assignments, answers to questions in the student handout, comments on the experiment, and lists of equipment, supplies, and reagents.
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*  Citation
 LeFevre, Joseph W. . J. Chem. Educ. 2000 77 361.
*  Keywords
 Chromatography; IR Spectroscopy; Laboratory Instruction; Natural Products; NMR Spectrometry
*  History
 Created:
Last Updated:		 February 14, 2000
August 31, 2005
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