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  Home > JCE Print > Journal of Chemical Education > Issues > 2009  > July  >
In the Laboratory
A Simple SN2 Reaction for the Undergraduate Organic Laboratory
John J. Esteb, John R. Magers, LuAnne McNulty, Paul Morgan, and Anne M. Wilson
Department of Chemistry, Butler University, Indianapolis, IN 46208
Cover
July 2009
Vol. 86 No. 7
p. 850
Abstract
A simple procedure for the synthesis of n-butyl naphthyl ether is presented. This procedure represents an easy method for the production of an aryl ether by an SN2 reaction, uses ethanol as an environmentally friendly solvent, and does not require the use of a lachrymator. Product isolation is done by pouring the reaction mixture over ice and collecting the solid by suction filtration. Students typically recover from 7–95% of the ether.
Supplement
Student handouts including pre- and postlab questions; Instructor notes including answers to the pre- and postlab questions and NMR spectra
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Contents
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JCE2009p0850W.doc (Microsoft Word)
 
More Information
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Citation
Esteb, John J.; Magers, John R.; McNulty, LuAnne; Morgan, Paul; Wilson, Anne M. J. Chem. Educ. 2009, 86, 850.
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Keywords
Acids / Bases; Alcohols; Ethers; Ethers; Hands-On Learning / Manipulatives; Laboratory Instruction; NMR Spectroscopy; Nucleophilic Substitution; Organic Chemistry; Phenols; Second-Year Undergraduate; Synthesis; Thin Layer Chromatography
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History
Created:
Last Updated:
6/1/2009
6/9/2009
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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