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Carbonium Ion Mechanism and Results of Solvolysis of (+)-2-Bromo-octane



THE remarkable prevalence of re-arrangement in simple alkyl groups during the formation of alkyl halides, and the concomitant loss in optical purity have been loosely ascribed to the intermediate formation of a carbonium cation1. The conversion of an alkyl halide into the alcohol, ester, or ether must therefore be scrutinized for points of correlation. There are few published examples of alkyl rearrangement in the solvolysis of straight chain alkyl halides. Isopropanol was formed in the mercury catalysed solvolysis of n-propyl bromide in aqueous formic acid, and the carbonium ion mechanism was postulated2.

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  1. 1

    Gerrard, W., and Hudson, H. R., J. Chem. Soc., 2310 (1964). Gerrard, W., Hudson, H. R., and Murphy, W. S., ibid., 2314 (1964).

  2. 2

    Coe, J. S., and Gold, V., J. Chem. Soc., 4940 (1960).

  3. 3

    Hughes, E. D., and Shapiro, U. G., J. Chem. Soc., 1192 (1937).

  4. 4

    Hughes, E. D., Ingold, C. K., and Masterman, S., J. Chem. Soc., 1196 (1937).

  5. 5

    Gates, P. N., Gerrard, W., and Mooney, E. F., J. Chem. Soc., 3480 (1964).

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