Related Experiment Video
Updated: Jul 17, 2026

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
Published on: October 18, 2018
Quantitative evaluation of the mechanism of electroreduction of benzoyl cyanides
Norma A Macías-Ruvalcaba1, Dennis H Evans
1Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Abstract:
The mechanism of reduction of benzoyl cyanide, 6, p-methoxybenzoyl cyanide, 7, and p-chlorobenzoyl cyanide, 8, has been studied in acetonitrile (6 and 7), N,N-dimethylformamide (6), and acetonitrile containing water (all three compounds). The reaction proceeds by initial reduction to form the anion radical followed by dimerization to produce an intermediate dianion, the dianion of the dicyanohydrin of benzil. The latter loses cyanide to give the anion of the monocyanohydrin of benzil, which undergoes two parallel reactions: expulsion of cyanide to give the corresponding benzil and rearrangement to the monoanion of mandelonitrile benzoate. The addition of water brings about an increase in the dimerization rate constant and an associated increase in the amount of benzil that is produced. The standard potentials for the initial reduction step have been evaluated, and their dependence on the substituent is discussed. The dimerization rate constants have also been evaluated.
More Related Videos
Related Concept Videos
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Electrophilic Aromatic Substitution: Nitration of Benzene
Reactions at the Benzylic Position: Oxidation and Reduction
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
