Abstract

The base-promoted elimination reactions of 2-(2,4,6-trinitrophenyl)ethyl halides in aqueous solution have been investigated. The relative rate constant ratios for elimination of fluoride, chloride, bromide, and iodide are 1:1.6:4.7:3.9, 1:1.9:4.3:8.5, and 1:2.2:10.2:14.7 for the hydroxide ion, trifluoroethoxide ion, and hexafluoroisopropoxide ion promoted reactions, respectively. This small spread in relative halogen leaving group abilities extends a previously reported trend of decreasing sensitivity to the identity of the leaving halogens as the β-aryl substituent is made more electron withdrawing in the series 2-phenylethyl, 2-(p-nitrophenyl)ethyl, 2-(2,4-dinitrophenyl)ethyl, and 2-(2,4,6-trinitrophenyl)ethyl halides. The fluoride to chloride rate constant ratio, however, shows little or no change for the 2-(2,4-dinitrophenyl)ethyl (2.0) and 2-(2,4,6-trinitrophenyl)ethyl (1.6) derivatives. The reactions are general-base promoted, with Bronsted β values increasing in the order 0.37:0.41:0.49:0.54 for the iodide, bromide, chloride, and fluoride substrates

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