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    • Kinetics and mechanism of oxidation of aliphatic alcohols by tetrabutylammonium tribromide

      Manju Baghmar Pradeep K Sharma

      Volume 113 Issue 2 April 2001 pp 139-146

    • Fulltext

       

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/113/02/0139-0146

    • Keywords

       

      Aliphatic alcohols; hydride ion transfer; tetrabutylammonium tribromide

    • Abstract

       

      Oxidation of nine primary aliphatic alcohols by tetrabutylammonium tribromide (TBATB) in aqueous acetic acid leads to the formation of the corresponding aldehydes. The reaction is first order with respect to TBATB. Michaelis-Menten type kinetics is observed with respect to alcohols. The reaction failed to induce the polymerization of acrylonitrile. Tetrabutylammonium chloride has no effect on the reaction rate. The proposed reactive oxidizing species is the tribromide ion. The oxidation of [1,1-2H2]ethanol exhibits a substantial kinetic isotope effect. The effect of solvent composition indicates that the rate increases with increase in the polarity of the solvent. The reaction is susceptible to both polar and steric effects of substituents. A mechanism involving transfer of a hydride ion in the rate-determining step has been proposed.

    • Author Affiliations

       

      Manju Baghmar1 Pradeep K Sharma1

      1. Department of Chemistry, JNV University, Jodhpur - 342 005, India

    • Dates

       
      Published
      April 2001
      Manuscript received
      20 May 2000
      Manuscript revised
      3 January 2001

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