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Conversion of an Alkyl Chloride to a Bromide (or Vice-Versa) by Homogeneous Nucleophile Exchange

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Roger C. Hahn

J. Chem. Educ., 1997, 74 (7), p 836

DOI: 10.1021/ed074p836

Publication Date (Web): July 1, 1997

Abstract

Quaternary salt-catalyzed bromide-chloride exchange between alkyl chlorides and alkyl bromides is used to demonstrate effects of temperature, catalyst, concentration, and substrate structure on reaction rates and chemoselectivity. Microscale reactions are monitored by GC analysis. In one experiment, a mixture of 1-chloropentane and 1-bromoheptane or of 1-bromopentane and 1-chloroheptane is equilibrated to form a mixture of all four compounds. In another experiment, bromide-chloride exchange between 1, 3-dichlorobutane and a large excess of 1-bromobutane demonstrates the greater S_N2 reactivity of a primary chloride relative to that of a secondary chloride.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Catalysis

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

A Safer, Discovery-Based Nucleophilic Substitution Experiment
Gail Horowitz
Journal of Chemical Education2009 86 (3), 363
- A Safer, Discovery-Based Nucleophilic Substitution Experiment
  Gail Horowitz
  Journal of Chemical Education2009 86 (3), 363
  A discovery-based nucleophilic substitution experiment is described in which students compare the reactivity of chloride and iodide ions in an SN2 reaction. This experiment improves upon the well-known "Competing Nucleophiles" experiment in that it does ...
  Abstract | Hi-Res PDF | PDF w/ Links
The State of Organic Teaching Laboratories
Gail Horowitz
Journal of Chemical Education2007 84 (2), 346
- The State of Organic Teaching Laboratories
  Gail Horowitz
  Journal of Chemical Education2007 84 (2), 346
  This review explores the dramatic changes that have taken place in the organic chemistry laboratory course over the last two to three decades. The most significant changes have been in the areas of pedagogy and technology. Significant inroads have been ...
  Abstract | Hi-Res PDF | PDF w/ Links