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19: More on Stereochemistry

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  • The fundamentals of structure and stereochemistry have been considered in previous chapters in some detail. There are, however, practical aspects of stereochemistry that have not yet been mentioned, particularly with regard to chiral compounds. How, for instance, can a racemic mixture be separated into its component enantiomers (resolution); what methods can be used to establish the configuration of enantiomers; how can we tell if they are pure; and how do we synthesize one of a pair of enantiomers preferentially (asymmetric synthesis)? In this chapter, some answers to these questions will be described briefly.

    Optical activity is an associated phenomenon of chirality and has long been used to monitor the behavior of chiral compounds. Brief mention of this was made earlier (Section 5-1C), but now the origin and measurement of optical rotation will be examined in more detail.

    Contributors and Attributions

    • John D. Robert and Marjorie C. Caserio (1977) Basic Principles of Organic Chemistry, second edition. W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, "You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format."