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The Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity

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R. David Crouch , Michael S. Holden and Candice A. Romany

Department of Chemistry, Dickinson College, Carlisle, PA 17013-2896

J. Chem. Educ., 2004, 81 (5), p 711

DOI: 10.1021/ed081p711

Publication Date (Web): May 1, 2004

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

NMR Spectroscopy

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