The Conversion of l-Phenylalanine to (S)-2-Hydroxy-3-phenylpropanoic Acid:: A Simple, Visual Example of a Stereospecific SN2 Reaction

• Nanine A. Van Draanen ^[1] ; Stephanie Hengst ^[1]
  1. [1] California Lutheran University

     California Lutheran University

     Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 87, Nº 6 (June), 2010, págs. 623-624
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • We report a simple, inexpensive, visual, and environmentally friendly SN2 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 1H NMR spectroscopy. The reaction converts readily available l-phenylalanine in a double SN2 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.