The iodochlorination of styrene, involving the addition of iodine monochloride to styrene, followed by the sodium methoxide-initiated dehydrohalogenation of the product results in a variable mixture of substituted styrenes by way of various substitution and elimination reaction mechanisms. As a result individual results are obtained for each student undertaking the experiment. The sequence of investigations associated with this laboratory exercise requires the application of mechanistic principles to explain the results as well as basic knowledge of GC–MS and NMR and the ability to apply this knowledge in combination to solve a problem. The exercise is to determine how many products are present and their relative proportions and to provide an opportunity to demonstrate how the branches of organic and analytical chemistry can contribute to the chemistry laboratory curriculum.

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