R. G. Stabile, A. Dicks
Oct 1, 2004
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0
Influential Citations
24
Citations
Journal
Journal of Chemical Education
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.