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Kinetics and mechanism of the oxidation of halotoluenes by acidic hexacyanoferrate(III)

✍ Scribed by A. K. Bhattacharjee; M. K. Mahanti

Publisher: John Wiley and Sons
Year: 1982
Tongue: English
Weight: 444 KB
Volume: 14
Category: Article
ISSN: 0538-8066
DOI: 10.1002/kin.550141005

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✦ Synopsis

Abstract

The oxidation of halotoluenes by hexacyanoferrate(III) in aqueous acetic acid containing perchloric acid (0.5__M__) at 50°C gave the corresponding aldehyde as the major product, and a small amount of polymeric material. The order with respect to each of the reactants—substrate, oxidant, and acid—was found to be unity. Increasing proportions of acetic acid increased the rate of the reaction. The reaction was influenced by changes in temperature, and the activation parameters have been evaluated. The Hammett plot yielded a ρ^+^ value of −1.8. A kinetic isotope effect k~H~/k~D~ = 6.0 has been observed. The pathway for the conversion of the halotoluenes to the products has been mechanistically visualized as proceeding through the benzylic radical intermediate, formed in the rate‐determining step of the reaction. The radical undergoes rapid conversion to the products.

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