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Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of alpha-Methylstyrene
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Department of Chemistry and Biochemistry, Bradley University, Peoria, IL 61625
J. Chem. Educ., 2008, 85 (1), p 102
DOI: 10.1021/ed085p102
Publication Date (Web): January 1, 2008
Abstract
In the described experiment, the regiochemical outcome of the addition of "HOBr" to α-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 α-methylstyrene and N-bromosuccinimide in 95% acetone (aq).
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Feature):
The Microscale LaboratoryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
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- Received: August 03, 2009
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