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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 10 Issue 5 (2005) pp 333-336

The Mechanism of the Bromination of Alkenes: The Beauty of Physical Organic Chemistry

Eric Bosch

Chemistry Department, Southwest Missouri State University, Springfield MO 65804,
Received February 1, 2005. Accepted March 11 2005.

Published online: 20 September 2005

Abstract. The history of the mechanism of the bromination of alkenes is presented with particular emphasis on the elegant experiments that have confirmed the formation of bromonium cation intermediates on reaction of alkenes with bromine. The independent characterization of bromonium cations using NMR spectroscopy and the ultimate X-ray crystallographic characterization of hindered bromonium cations are highlighted.

Key Words: Laboratories and Demonstrations; organic chemistry; bromination; alkene; mechanism; bromonium ion; steric hinderance; resonance stabilization; X-ray crystallography; NMR spectroscopy

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Issue date: October 1, 2005

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