Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of alpha-Methylstyrene.

• Autores: Brad Andersh, Kathryn N. Kilby, Meghan E. Turnis, Drew L. Murphy
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 85, Nº 1, 2008, págs. 102-103
• Idioma: inglés
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• Resumen

  • In the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition. As expected, 1-bromo-2-phenyl-2-propanol is the major product from the reaction of a-methylstyrene and N-bromosuccinimide in 95% acetone (aq).