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Regioselective Hydrochlorination: An Experiment for the Undergraduate Laboratory

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Philip Boudjouk , Beon-Kyu Kim and Byung-Hee Han

North Dakota State University, Department of Chemistry, Fargo, ND 58105

J. Chem. Educ., 1997, 74 (10), p 1223

DOI: 10.1021/ed074p1223

Publication Date (Web): October 1, 1997

Section:

History, Education, and Documentation

Abstract

A simple and convenient procedure for the addition of hydrogen chloride to a variety of olefins is described. Trimethylchlorosilane and water are used to generate the hydrogen chloride in the presence of the olefin to produce the desired chloride in high yield. Regioselectivity is high: electrophilic addition dominates for simple olefins and nucleophilic addition prevails for alpha,beta - unsaturated olefins. Conventional glassware is used and product isolation is straightforward using distillation techniques.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Learning Theories

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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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