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Phase Transfer Catalytic Reactions: A Physical Chemistry Laboratory Experiment

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Nahid Shabestary , Sadegh Khazaeli and Richie Hickman

Department of Chemistry, Southern Illinois University at Edwardsville, Edwardsville, IL 62026

J. Chem. Educ., 1998, 75 (11), p 1470

DOI: 10.1021/ed075p1470

Publication Date (Web): November 1, 1998

Section:

History, Education, and Documentation

Abstract

This article describes the application of phase-transfer catalysis within an undergraduate physical chemistry laboratory. Phase-transfer catalysis has been covered extensively in various books, articles, and patents. Many important industrial products are manufactured using this technique. However, very little of the subject is reflected in current undergraduate curriculum. The kinetic experiment designed here introduces many important concepts in phase-transfer catalysis and nucleophilic displacement reactions involving both mechanism and kinetics. Since this laboratory exploration includes catalytic reactions, organic synthesis, and chemical analysis, it covers many areas of chemistry. Thus, we believe this can be an important contribution to the students' learning.In this experiment, we have demonstrated that the reactions of alkyl bromides with NaCl under phase-transfer conditions can be carried out replacing bromide with chloride via a nucleophilic displacement reaction within a three-hour physical chemistry laboratory period.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Physical Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Equilibrium

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

Modern Developments in the Physical Chemistry Laboratory
Samuel A. Abrash
2007 973 (), 115-151
- Modern Developments in the Physical Chemistry Laboratory
  Samuel A. Abrash
  2007 973 (), 115-151
  Developments in the physical chemistry laboratory since the publication of the germinal text by Schwenz and Moore (1) are categorized and reviewed. The categories examined include modern instrumentation, current topics in chemistry, integrated ...
  Abstract | Hi-Res PDF | PDF w/ Links
Colorful Chemical Demonstrations on the Extraction of Anionic Species from Water into Ether Mediated by Tricaprylylmethylammonium Chloride (Aliquat 336), a Liquid–Liquid Phase-Transfer Agent
Patrick Gordon , Anil Joseph Pezhathinal , Kerensa Rocke , Louis Susanto , Derek Handke and Roch Chan-Yu-King , Eugene N. Losey , Richard L. Keiter
Journal of Chemical Education2006 83 (8), 1161
- Colorful Chemical Demonstrations on the Extraction of Anionic Species from Water into Ether Mediated by Tricaprylylmethylammonium Chloride (Aliquat 336), a Liquid–Liquid Phase-Transfer Agent
  Patrick Gordon , Anil Joseph Pezhathinal , Kerensa Rocke , Louis Susanto , Derek Handke and Roch Chan-Yu-King , Eugene N. Losey , Richard L. Keiter
  Journal of Chemical Education2006 83 (8), 1161
  Liquid–liquid phase transfer catalysis (LLPTC) plays an ever-increasing role in academic research and in the large scale industrial production of chemicals. This method involves a biphasic medium composed of water and an organic solvent in which the LLPT-...
  Abstract | Hi-Res PDF | PDF w/ Links
The Base-Induced Reaction of Salicylaldehyde with 1-Bromobutane in Acetone: Two Related Examples of Chemical Problem Solving
Holly D. Bendorf and Chriss E. McDonald
Journal of Chemical Education2003 80 (10), 1185
- The Base-Induced Reaction of Salicylaldehyde with 1-Bromobutane in Acetone: Two Related Examples of Chemical Problem Solving
  Holly D. Bendorf and Chriss E. McDonald
  Journal of Chemical Education2003 80 (10), 1185
  This investigational laboratory experiment emphasizes structure determination using modern spectroscopic techniques. The experiment examines the base-induced reaction of salicylaldehyde with 1-bromobutane in acetone. The product obtained from the reaction ...
  Abstract | Hi-Res PDF | PDF w/ Links