Solvated Electrons in Organic Chemistry Laboratory

• Predrag Peter Ilich ^[1] ; Kathleen R. McCormick ^[1] ; Adam D. Atkins ^[1] ; Geoffrey J. Mell ^[1] ; Timothy J. Flaherty ^[1] ; Martin J. Bruck ^[1] ; Heather A. Goodrich ^[1] ; Aaron L. Hefel ^[1] ; Nenad Juranic ^[3] ; Suzanne Seleem ^[2]
  1. [1] Loras College

     Loras College

     City of Dubuque, Estados Unidos

     
  2. [2] Central State University

     Central State University

     Township of Xenia, Estados Unidos

     
  3. [3] Mayo Foundation, Rochester

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• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 87, Nº 4 (April), 2010, págs. 419-422
• Idioma: inglés
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• Resumen

  • A novel experiment is described in which solvated electrons in liquid ammonia reduce a benzyl alcohol carbon without affecting the aromatic ring. The reductive activity of solvated electrons can be partially or completely quenched through the addition of electron scavengers to the reaction mixture. The effectiveness of these scavengers was found to qualitatively correlate with their electron affinities obtained from first-principles electronic-structure calculations. The reaction completion is monitored using 13C NMR spectroscopic analysis of the whole reaction mixture, without separation and purification. This interesting, dynamic, and diverse experiment combines a classical synthetic procedure, NMR spectroscopy, and molecular modeling and is suitable for second-year through fourth-year chemistry and biochemistry majors.