ERIC Number: EJ918273
Record Type: Journal
Publication Date: 2010-Jun
Pages: 2
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Available Date: N/A
The Conversion of L-Phenylalanine to ("S")-2-Hydroxy-3-Phenylpropanoic Acid: A Simple, Visual Example of a Stereospecific S[subscript N]2 Reaction
Van Draanen, Nanine A.; Hengst, Stephanie
Journal of Chemical Education, v87 n6 p623-624 Jun 2010
We report a simple, inexpensive, visual, and environmentally friendly S[subscript N]2 reaction appropriate for the second-year organic chemistry laboratory that illustrates stereospecificity, dependence of water solubility on the state of ionization, optical activity, and effect of diastereotopic protons in [superscript 1]H NMR spectroscopy. The reaction converts readily available l-phenylalanine in a double S[subscript N]2 reaction to enantiomerically pure ("S")-2-hydroxy-3-phenylpropanoic acid. The optical purity and absolute stereochemistry are determined by the specific rotation of the product. (Contains 1 figure, 1 scheme and 1 note.)
Descriptors: Organic Chemistry, Science Instruction, College Science, Undergraduate Study, Science Laboratories, Molecular Structure, Teaching Methods, Scientific Principles
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A
Author Affiliations: N/A