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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > May  >
In the Laboratory
The Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity
R. David Crouch, Michael S. Holden, and Candice A. Romany
Department of Chemistry, Dickinson College, Carlisle, PA 17013-2896
Cover
May 2004
Vol. 81 No. 5
p. 711
Abstract
The Darzens condensation involves two steps that are typically included in the sophomore organic curriculum: an aldol reaction followed by an intramolecular nucleophilic substitution. The resulting epoxide can form cis or trans diastereomers. In this experiment, students draw on their understanding of the possible reactions of the substrates and an analysis of the NMR spectrum of the product to determine the product structure and arrive at a mechanism to explain its formation. Integration of the NMR signals allows the ratio of cis and trans isomers to be determined and coupling constants allow the major product to be identified.
Supplement
Instructions for the students, notes for the instructor, and sample 1H NMR spectra of the product are available.
*  Contents Folder JCE2004p0711W containing JCE2004p0711W.doc (Microsoft Word); F0330096.cdx, F04030096.cdx (ChemDraw); F05030096.jpg, and F06030096.jpg
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*  Citation
 Crouch, R. David; Holden, Michael S.; Romany, Candice A. J. Chem. Educ. 2004 81 711.
*  Keywords
 Laboratory Instruction; NMR Spectrometry; Organic Chemistry; Organic Synthesis; Stereochemistry
*  History
 Created:
Last Updated:		 April 1, 2004
February 18, 2005
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