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Kinetics and mechanism of oxidation of some aliphatic esters by sodium N-bromo-p-toluenesulfonamide

✍ Scribed by K. S. Rangappa; C. K. Mythily; D. S. Mahadevappa; N. M. Made Gowda

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
477 KB
Volume
25
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The kinetics of oxidation of methyl, ethyl, n‐propyl, isopropyl, and n‐butyl acetates to acetic acid and the corresponding aldehyde by the title oxidant in aqueous HCl medium at 40°C has been studied. The reaction shows first‐order with respect to [oxidant] and fractional orders in [H^+^] and [ester]. An isokinetic relationship was observed with β = 374 K indicating enthalpy as the rate controlling factor. Attempts have been made to arrive at a linear free energy relationship through the Taft treatment. Electron releasing groups in the ester moiety increase the rate with ρ* = −9.88. A two‐pathway mechanism, consistent with the observed kinetic data, has been proposed. © 1993 John Wiley & Sons, Inc.

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