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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > October  >
In the Laboratory
The Microscale Laboratory
Two-Step Semi-Microscale Preparation of a Cinnamate Ester Sunscreen Analog
Ryan G. Stabile and Andrew P. Dicks
Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada
Cover
October 2004
Vol. 81 No. 10
p. 1488
Abstract
The two-step synthesis and characterization of a sunscreen analog (ethyl trans-4-methoxycinnamate) is presented. This experiment is tailored towards students with a sound theoretical understanding of organic chemistry and related laboratory techniques. Appropriate synthetic discussion topics include carbonyl condensation reactions, carboxylic acid esterifications, and the so-called "cesium effect" in organic synthesis. Product geometry may be concealed and deduced by spectroscopic analysis. The product 1H NMR spectrum reinforces classical concepts of electronic shielding–deshielding effects and proton coupling. Students are able to connect the structure of ethyl trans-4-methoxycinnamate with its ability to act as an ultraviolet light absorber.

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Supplement
Instructions for the students, notes for the instructor, and spectroscopic information are available.
*  Contents JCE2004p1488W.doc (Microsoft Word)
 
*  Download



 
More Information
*  Citation
 Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2004 81 1488.
*  Keywords
 Consumer Chemistry; IR Spectroscopy; Laboratory Instruction; Mechanisms; Microscale; NMR Spectrometry; Organic Chemistry; Organic Synthesis; UV-Vis Spectroscopy
*  History
 Created:
Last Updated:		 August 31, 2004
September 8, 2004
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