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Synthesis of a Bromohydrin: An Experiment Demonstrating Markovnikov Addition
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Abstract
The fundamental principle of regiospecific electrophilic addition to alkenes is Markovnikov's rule. Despite the significance of this principle, the only reported experiment for the organic chemistry laboratory that demonstrates Markovnikov addition is oxymercuration, an experiment that has the unfavorable aspect of generating mercury metal. We have developed a microscale experiment based on the bromohydrin derived from 1-methylcyclohexene which alleviates the generation of noxious material yet demonstrates, unequivocally, the fundamental concepts of Markovnikov addition. Synthesis, purification, and product characterization using both instrumental methods and qualitative analysis are presented.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of alpha-Methylstyrene
Brad Andersh , Kathryn N. Kilby , Meghan E. Turnis and Drew L. MurphyJournal of Chemical Education2008 85 (1), 102Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of alpha-Methylstyrene
Brad Andersh , Kathryn N. Kilby , Meghan E. Turnis and Drew L. MurphyJournal of Chemical Education2008 85 (1), 102In 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 ...
Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a beta-Bromostyrene
Thomas A. EvansJournal of Chemical Education2006 83 (7), 1062Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a beta-Bromostyrene
Thomas A. EvansJournal of Chemical Education2006 83 (7), 1062The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. The product is purified by dry column vacuum chromatography and its ...
Iodolactonization of 4-Pentenoic Acid
R. David Crouch , Alexander Tucker-Schwartz and Kathryn BarkerJournal of Chemical Education2006 83 (6), 921Iodolactonization of 4-Pentenoic Acid
R. David Crouch , Alexander Tucker-Schwartz and Kathryn BarkerJournal of Chemical Education2006 83 (6), 921An experiment in which 4-pentenoic acid is converted into a lactone via iodolactonization is described. In this lab activity, the alkenoic acid is treated with I2 prepared in situ, forming an iodonium ion that undergoes intramolecular nucleophilic attack ...
Moving Past Markovnikov's Rule
E. Eugene GoochJournal of Chemical Education2001 78 (10), 1358Moving Past Markovnikov's Rule
E. Eugene GoochJournal of Chemical Education2001 78 (10), 1358A broadened application of Markovnikov's rule is proposed that virtually eliminates the common exceptions that cause students difficulty. Alkene addition mechanisms can be an excellent case study showing how empirical rules evolve into more advanced ...
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- Received: August 03, 2009
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