Solvated Electrons in Organic Chemistry Laboratory

Abstract

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.