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Regioselective Methoxybromination of Styrene Using TBABr3 in Methanol: An Organic Laboratory Experiment

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Jacques Berthelot , Yamina Benammar and Catherine Lange

Universite Pierre et Marie Curie, Laboratoire de Chimie Organique Structurale 2, CNRS, ERS 72, Boite 45, 4 Place Jussieu, 75252 Paris Cedex 05, France

J. Chem. Educ., 1995, 72 (9), p 850

DOI: 10.1021/ed072p850

Publication Date: September 1995

Abstract

An organic laboratory experiment using tetrabutylammonium tribromide (TBABr3) and styrene in methanol under mild conditions is reported. The Markovnikov type regioisomer of the methoxybromo adduct was obtained in high yield.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis

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This article has been cited by 1 ACS Journal articles (1 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. Murphy
Journal of Chemical Education2008 85 (1), 102
- Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of alpha-Methylstyrene
  Brad Andersh , Kathryn N. Kilby , Meghan E. Turnis and Drew L. Murphy
  Journal of Chemical Education2008 85 (1), 102
  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 ...
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