The role of tetraalkylammonium salts in the electro‐reduction of ketones. I. Competitive adsorption in an aqueous medium

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Abstract
Aryl alkyl ketones and tetraalkylammonium ions compete for adsorption in the region where the adsorption voltage ranges of the respective compounds overlap. A study has been made of the effects of changes in structure of the tetraalkylammonium salts as well as of the ketones, of the nature of the anion and of the polarity of the medium on this competitive adsorption. It is concluded that in the presence of tetraalkylammonium ions the reduction of a corbonyl compound occurs on top of an adsorbate layer of such ammonium ions. Consequences of the results reported with respect to the mechanism of asymmetric induction in carbonyl reduction and of the mechanism of electropinacolization are discussed.