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The chromic acid oxidation of aliphatic secondary alcohols—substituent effects and the mechanism

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Abstract

The mechanism of the chromic acid oxidation of a number of substituted propan-2-ols has been studied in aqueous acetic acid medium. Electron withdrawing substituents retard the reaction considerably while electron-releasing substituents accelerate the reaction. A good correlation exists between the rate and σ* values. The ρ* value is −1.60. The results are interpreted in terms of a rate-determining abstraction of the secondary hydrogen as a hydride anion.

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Authors and Affiliations

  1. Department of Chemistry, Vivekananda College, Madras-4

    N. Venkatasubramanian & G. Srinivasan

Authors
  1. N. Venkatasubramanian
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  2. G. Srinivasan
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Communicated by Prof. S. V. Anantakrishnan,f.a.sc.

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Venkatasubramanian, N., Srinivasan, G. The chromic acid oxidation of aliphatic secondary alcohols—substituent effects and the mechanism. Proc. Indian Acad. Sci. 71, 1–8 (1970). https://doi.org/10.1007/BF03050446

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  • DOI: https://doi.org/10.1007/BF03050446

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