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The Addition of Hydrogen Bromide to Simple Alkenes

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Hilton M. Weiss

Bard College, Annandale-on-Hudson, NY 12504

J. Chem. Educ., 1995, 72 (9), p 848

DOI: 10.1021/ed072p848

Publication Date: September 1995

Abstract

This experiment describes the addition of HBr (in acetic acid) to a series of simple alkenes. NMR analysis of the products shows ionic addition with alkenes capable of forming tertiary carbocations, whereas other alkenes give anti-Markovnikov products. Preemptive destruction of peroxides allows the slow ionic addition to the latter alkenes.A preparative scale synthesis of 1-bromohexane is also described.

Keywords (Audience):

Second-Year 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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