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
J. Chem. Educ., 2009, 86 (7), p 850
DOI: 10.1021/ed086p850
Publication Date (Web): July 1, 2009
History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Acids / Bases
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  • Received: August 03, 2009

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