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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 15 (2010) pp 247-250

A Laboratory Demonstration of Synthesis of Bromoalkanes: Free Radical Bromination of an Alkylbenzene and Addition of Hydrogen Bromide to an Alkene

Karenia Soto and Veljko Dragojlovic*

Wilkes Honors College of Florida Atlantic University, 5353 College Drive, Jupiter, FL 33458,
Received March 4, 2008. Accepted May 9, 2009.

Published: 23 June 2010

Abstract. A relatively simple experimental set up allows for both a free radical bromination of tetralin and addition of hydrogen bromide to 3,3-dimethyl-1-butene to be simultaneously carried out. Both reactions had, for the students, unexpected outcome with the major products being naphthalene, 1-bromonaphthalene and 1,4-dibromonaphthalene while addition of hydrogen bromide to 3,3-dimethyl-1-butene gave as the major reaction product either 1-bromo-3,3-dimethylbutane or 2-bromo-2,3-dimethylbutane, depending on the reaction conditions. Students were provided with description of the reaction outcome from different literature sources and asked to evaluate them.

Key Words: Laboratories and Demonstrations; organic chemistry

(*) Corresponding author. (E-mail:

Article in PDF format (182 KB) HTML format

Supporting Materials:

A list of chemicals and supplies, additional experimental details, movies (wav files) of the demonstration and Student Handout are available as supporting material. Gas chromatograms of each reaction as well as mass spectra of the products are provided as a PDF file. (1.14 MB)

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