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Mechanisms for Liquid Phase Hydrolyses of Chlorobenzene and Halotoluenes

Bottini, Albert T. and Roberts, John D. (1957) Mechanisms for Liquid Phase Hydrolyses of Chlorobenzene and Halotoluenes. Journal of the American Chemical Society, 79 (6). pp. 1458-1462. ISSN 0002-7863. doi:10.1021/ja01563a050.

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A study of the rearrangements which occur during the high temperature liquid phase hydrolyses of the halotoluenes has shown that the extent of rearrangement is a sensitive function of temperature, base strength and the nature of the halogen. These hydrolyses involve either a benzyne (elimination-addition) mechanism, which gives both rearranged and unrearranged products, or an S_N2-type mechanism. The S_N2-type mechanism was found to be favored at lower temperatures, in the presence of weaker bases and with the more easily ionizable halogens. By suitable choice of conditions, one or the other reaction could be made to occur almost exclusively. Chlorobenzene-1-^(14)C, with 4 M sodium hydroxide solution at 340º, gave 58 ± 1% phenol-1-^(14)C and 42 ± 1% phenol-2-^(14)C, which indicates that under these conditions the benzyne mechanism predominates but is not the exclusive reaction path.

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Additional Information:© 1957 American Chemical Society. Received September 4, 1956. Presented in part at the National Academy of Science Meeting in Pasadena, California, November 4, 1955; J. D. Roberts, A. T. Bottini and D. A. Semenow, Science, 122, 881 (1955). National Science Foundation Predoctoral Fellow, 1954-1957.
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NSF Predoctoral FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2131
Issue or Number:6
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Official Citation:Mechanisms for Liquid Phase Hydrolyses of Chlorobenzene and Halotoluenes Albert T. Bottini and John D. Roberts Journal of the American Chemical Society 1957 79 (6), 1458-1462 DOI: 10.1021/ja01563a050
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ID Code:61350
Deposited On:21 Oct 2015 19:42
Last Modified:10 Nov 2021 22:47

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