The Competitive Reaction of Nucleophiles in the Butanol Series Revisited

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 18 (2013) pp 001-005
DOI 10.1007/s00897132454a

The Competitive Reaction of Nucleophiles in the Butanol Series Revisited

Nabyl Merbouh*, Paul R. C. Saunders, Greg Gaube, Colin Zhang, and Andrew R. Lewis*

Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC V5A 1S6, Canada, nmerbouh@sfu.ca, arl@sfu.ca
Received August 23, 2012. Accepted October 26, 2012.

Published: 26 January 2013

Abstract. An improved procedure for the study of the competitive reaction of nucleophiles in the butanol series is described. Starting with 1-butanol, 2-butanol and 2-methyl-2-propanol, the relative nucleophilicities of chloride and bromide ions during a nucleophilic substitution reaction are examined by automated ¹H-NMR spectroscopy instead of the usual gas chromatography. While the reaction time, purification and extraction procedures were slightly modified and simplified to accommodate a large laboratory group (60 students); the data acquisition time was shortened considerably by use of the ¹H-NMR method. Furthermore, the cost of the experiment per student was reduced significantly.

Key Words: Laboratories and Demonstrations; organic chemistry

(*) Corresponding author. (E-mail: nmerbouh@sfu.ca, arl@sfu.ca )

Article in PDF format (177 KB) HTML format

Supporting Materials:

Includes GC data,300, 400 and 500 MHzNMR spectra, and a description of the steps and files required to implement the automated procedure on a Bruker NMR spectrometer. For NMR parameter sets and more details of the scripts, please contact Dr. Andrew Lewis (4.6 MB)