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

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

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, gbreton@berry.edu
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: gbreton@berry.edu)

Article in PDF format (174 KB) HTML format

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).