Dynamic Stereochemistry: A Simple Approach To Delineating Relative Configuration

Dipak K. Mandal
Department of Chemistry, Presidency College, Kolkata 700 073, India
J. Chem. Educ., 2007, 84 (2), p 274
DOI: 10.1021/ed084p274
Publication Date (Web): February 1, 2007
History, Education, and Documentation

Abstract

The stereochemistry of reactions at a tetrahedral center in organic molecules primarily involves inversion or retention of configuration at that center. In this context, a simple approach is presented for delineating relative stereochemistry of the product in reactions involving stereogenic center(s). The configuration at a tetrahedral center is defined by a pair of ligands related by a clockwise (or counterclockwise) arc and a front (or rear) ligand. The arc is drawn through the tetrahedral angle taking the tetrahedral center as the geometric center. The inversion or retention of configuration is assigned by examining whether the clockwise–counterclockwise and front–rear relationships of two ligand pairs in the starting material are maintained or changed in the product. One change of such relationship would lead to inversion while retention involves either no change or changes of both the relationships. The method is illustrated with suitable examples.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Mnemonics / Rote Learning

Keywords (Subject):

Chirality / Optical Activity
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  • Received: August 03, 2009

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