We have adapted the dehydration of 2-methyl-2-propanol to a "puzzle" approach for use in our second-semester chemistry major organic laboratory. The reaction of 2-methyl-2-propanol with ˜50% sulfuric acid at 100 °C yields isobutylene, which reacts further by a "puzzling" reaction. By coupling the GC–MS analysis of the product mixture with their knowledge of the mechanism of alcohol dehydration and alkene reactivity, students are able to identify the major products of this reaction.
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Citation
Pelter, Michael W.; Macudzinski, Rebecca M. J. Chem. Educ.1999, 76, 826.
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