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ERIC Number: EJ918273
Record Type: Journal
Publication Date: 2010-Jun
Pages: 2
Abstractor: As Provided
Reference Count: 3
ISSN: ISSN-0021-9584
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.)
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:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A