Open Access Peer-reviewed

Microwave-Assisted Esterifications: An Unknowns Experiment Designed for an Undergraduate Organic Chemistry Laboratory

Jessica S. Lampkowski1, William Bass1, Zachary Nimmo1, Douglas D. Young1,

1Department of Chemistry, College of William & Mary, Williamsburg, VA, USA

World Journal of Chemical Education. 2015, 3(5), 111-114. DOI: 10.12691/wjce-3-5-1
Published online: August 25, 2017

Abstract

The utilization of microwaves in synthetic chemistry provides a mechanism for the efficient heating of reactions, offering benefits such as rapid reaction rates and increased yields. Here, we present an undergraduate organic chemistry lab that utilizes microwave technology to perform esterification with alcohol unknowns. This experiment would normally require over an hour for reflux and apparatus assembly; however, with microwave technology we are able to develop a generic methodology to accomplish the esterification reaction in five minutes, demonstrating the efficiency of the microwave and allowing more time for product analysis and characterization. Moreover, the integration of an unknowns aspect to the laboratory implements the problem-solving laboratory approach and confers the ability to solidify principles of NMR spectroscopy as well as product purification techniques.

Keywords:

undergraduate laboratory experiment, hands-on learning, microwave irradiation, esterification
[1]  Hoz, A.; Loupy, A. Eds. Microwaves in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2012.View Article
 
[2]  Herrero, M.A.; Kremsner, J.M.; Kappe, C.O. Nonthermal Microwave Effects Revisited: On the Importance of Internal Temperature Monitoring and Agitation in Microwave Chemistry. J. Org. Chem. 2008, 73, 36-47.View Article  PubMed
 
[3]  Reilly, M.K.; King, R.P.; Wagner, A.J.; King, S.M. Microwave-Assisted Esterification: A Discovery-Based Microscale Laboratory Experiment. J. Chem. Educ. 2014. 91, 1706-1709.View Article
 
[4]  Wilson, H. Problem-Solving Laboratory Excercises. J. Chem. Educ. 1987. 64, 895-896.View Article
 
[5]  Browne, L.M.; Blackburn, E.V. Teaching Introductory Organic Chemistry: A Problem-Solving and Collaborative Learning Approach. J. Chem. Educ. 1999. 76, 1104-1107.View Article
 
[6]  (a) Bromfield-Lee, D. C.; Oliver-Hoyo, M. T.An Esterification Kinetics Experiment That Relies on the Sense of Smell J. Chem. Educ. 2009, 86, 82-84 (b) Birney, D. M.; Starnes, S.D. Parallel Combinatorial Esterification: A Simple Experiment for Use in the Second-Semester Organic Chemistry Laboratory J. Chem. Educ. 1999, 76, 1560-1561 (c) Wade, P. A.; Rutkowsky, S. A.; King, D. B.A Simple Combinatorial Experiment Based on Fischer Esterification. An Experiment Suitable for the First-Semester Organic Chemistry Lab J. Chem. Educ. 2006, 83, 927-928.
 
[7]  Bauer, K.; Garbe, D. Common Fragrances and Flavor Materials: Preparation, Properties, and Uses; VCH: Weinheim, 1985.
 
[8]  Leadbeater, N.; McGowan, C. Experiment 2−Esterification. In Clean, Fast, Organic Chemistry: Microwave-Assisted Laboratory Experiments; CEM Publishing: Matthews, NC, 2006; pp 5-59.