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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > October  >
In the Laboratory
A Discovery-Based Friedel–Crafts Acylation Experiment: Student-Designed Experimental Procedure
Anne McElwee Reeve
Chemistry Program, School of Science, Lynchburg College, Lynchburg, VA 24501
Cover
October 2004
Vol. 81 No. 10
p. 1497
Abstract
A discovery-based Friedel–Crafts acylation experiment that includes a student-designed procedure, spectroscopic analysis of an unknown aromatic product, and molecular modeling is described. Students design the synthetic procedure and workup for the acylation of an unknown aromatic starting material in an instructor-guided classroom discussion that integrates concepts from the first semester of organic lab into a new context. The reaction proceeds in 50–85% isolated yield following a simple extractive workup. 1H NMR spectroscopy is used to identify the para-substituted acetophenone product, which leads to the identification of the starting material. Semi-empirical calculations are performed on molecular models of the ortho- and para-substituted acetophenone isomers to assess the thermodynamic stability of each, providing an explanation for the lack of ortho isomer in the reaction.
Supplement
Instructor notes and class discussion guidelines, results of student-designed procedure (as a formal handout), molecular modeling instructions, and the CAS numbers of all compounds are available.
*  Contents JCE2004p1497W.doc (Microsoft Word)
 
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More Information
*  Citation
 Reeve, Anne McElwee. J. Chem. Educ. 2004 81 1497.
*  Keywords
 Aromaticity / Aromatics; Chromatography; Inquiry-Based / Discovery Method; IR Spectroscopy; Laboratory Instruction; Molecular Modeling / Dynamics; NMR Spectrometry; Organic Synthesis
*  History
 Created:
Last Updated:		 August 31, 2004
September 8, 2004
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