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.

Carbon Particle-Doped Polymer Layers on Metals as Chemically and Mechanically Resistant Composite Electrodes for Hot Electron Electrochemistry

“…Hot-and hydrated/solvated electrons can be easily obtained with these electrodes in any laboratory to induce various one-electron reductions in aqueous solutions not obtainable at active metal electrodes on the basis of traditional electrochemistry. For instance, metal ions at unusual oxidation states not obtainable at active metal electrodes can be created at the present composite electrodes as in the case in pulse radiolysis [24], many types of luminophores can be excited by reaction cycles involving one-electron redox steps [1][2][3][4][5]. Different types of organic pollutants can be disintegrated by hot and hydrated electrons [5,32,[44][45][46]; also some specific organic synthesis can be carried out with hydrated electrons [47].…”

“…Our group has utilized hot electron injection into aqueous solution only in generating hot electroninduced electrochemiluminescence (HECL) of our labels for bioaffinity assays, but there are many other application areas for hot electron electrochemistry. Solvated electrons can be utilized in organic chemistry [24] and in inorganic chemistry [25,26] and e.g. in disinfection of potable water and treatment of waste waters [27][28][29].…”

Readily Made Solvated Electrons

“…A similar generator was used by Ilich and co-workers. 7 ABSTRACT: The existence of solvated electrons has been known for a long time. Key methods for their production (i.e., photoionization of reducing ions, water radiolysis, and the reaction between H 3 and OH -) are unsuitable for most school laboratories.…”

“…Other coolants may be tried as well, for example, dry ice with acetone, 16 2-propanol, 17 CaCl 2 , 18 o-xylene/ m-xylene, 19 or 2-butanol. 7 To produce gaseous NH 3 , heat the sand bath to at least 40 °C. To aid the process, a couple of NaOH pellets can be added to the concentrated aqueous ammonia (see discussion section below).…”

Synthesis and Characterization of Biphenyl-Based Lithium Solvated Electron Solutions

“…Till today, the most commonly known solvated electron solutions are those formed by dissolution of lithium in liquid ammonia. Solvated electron solutions are often described in a range of synthesis methods − as well for use in a range of possible applications and research fields. − …”