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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 10 Issue 4 (2005) pp 298-299

Free Radical Bromination of 2-Methylbutane and Analysis by 1H NMR Spectroscopy

Gary W. Breton

Berry College, Department of Chemistry, PO Box 495016, Mount Berry, GA 30149,
Received March 17, 2005. Accepted May 2, 2005.

Published online: 15 June 2005

Abstract. The free-radical bromination of inexpensive 2-methylbutane using neat Br2 takes place smoothly using a conveniently designed microscale glassware setup to provide a single major product. This product is readily identified as 2-bromo-2-methylbutane by comparison of the observed 1H NMR spectrum to spectra predicted for each of the potential products. This laboratory experiment demonstrates the powerful use of 1H NMR spectroscopy as a means for identification of a major reaction product from the spectrum of a crude reaction mixture.

Key Words: Laboratories and Demonstrations; organic chemistry; synthesis

(*) Corresponding author. (E-mail:

Article in PDF format (174 KB) HTML format

Supporting Materials:


Supporting Materials:

Supporting materials available in a Zip file include the student handout for the laboratory experiment, a chart for prediction of approximate 1H NMR chemical shifts, the 1H NMR and IR spectra of bromide 2, and JPEG pictures of the irradiation process and irradiation setup. (340 KB).

Issue date: August 1, 2005

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