A novel approach to exploring Hammett relationships in the undergraduate teaching lab is described. The use of competition experiments proved to be a reliable method for the construction of Hammett plots with good correlation. Reactions that were studied include the sodium borohydride reduction, methylmagnesium bromide addition, and oxime formation with para-substituted acetophenones. The composition of reaction mixtures was established by 1 H NMR integrations. The use of competition experiments ensured consistency in the results, as relatively little control was required over the reaction conditions. Thus, this method provides great flexibility with regard to the compounds and reactions that may be studied.
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Mullins et al. (2004) studied this question.
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