Reactions of Organic Halides in Solution


REACTIONS of organic halides in solution which involve substitution by a nucleophilic reagent at a saturated carbon atom have been extensively studied by Hughes, Ingold and co-workers1. These authors conclude that reactions of this type may occur by two possible mechanisms, a unimolecular mechanism S N 1 or a bimolecular mechanism S N 2 . The increase in the unimolecular S N 1 reaction-rate of the halide RX as R varies along the series methyl, ethyl, sec.-propyl, tert.butyl, is attributed by these authors to the increase in electron accession to the reaction centre2. The decrease in the bimolecular S N 2 reaction-rate along this series3 is also attributed to the increase in electron accession to the reaction centre ; this electron accession is assumed to inhibit the approach of the nucleophilic reagent.

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    Ingold and Rothstein, J. Chem. Soc., 1217 (1928). Hughes, Ingold and Patel, J. Chem. Soc., 526 (1933). For further references see "General Discussion on Mechanism of Organic Reactions in Liquid Systems", Trans. Farad. Soc., 37, 601 (1941).

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    Bateman and Hughes, J. Chem. Soc., 945 (1940).

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    Bateman, Cooper, Hughes and Ingold, J. Chem. Soc., 925 (1940).

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    Ogg and Polanyi, Trans. Farad. Soc., 31, 604 (1935).

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    Baughan, Evans, M. G., and Polanyi, Trans. Farad. Soc., 37, 377

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    Hippie and Stevenson, Phys. Rev., 63, 121 (1943).

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    Hippie and Stevenson, J. Amer. Chem. Soc., 64 1590, 2766, 2769 (1942).

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    Hughes, Trans. Farad. Soc., 37, 603 (1941).

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    Young and Andrews, J. Amer. Chem. Soc., 66, 421 (1944).

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EVANS, A. Reactions of Organic Halides in Solution. Nature 157, 438–439 (1946) doi:10.1038/157438c0

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