COMPUTER-ASSISTED MECHANISTIC EVALUATION OF ORGANIC REACTIONS
Abstract
An interactive computer program has been developed to predict the products of organic reactions given starting materials and reaction conditions. The program has been named CAMEO, for computer-assisted mechanistic evaluation of organic reactions. In contrast to earlier approaches, analyses proceed in the forward, or synthetic, direction and the prediction of products is based on the internal evaluation of mechanistic pathways. This thesis covers graphics, perception and base-catalyzed mechanisms, which are the principle segments in CAMEO. Mechanisms are further divided into organometallic and nonorganometallic processes. The program draws upon the chemsists' knowledge through the use of interactive computer graphics. Organizing principles have been developed to govern competition among the constituent mechanistic pathways--proton, transfer, halogen-metal exchange, addition, substitution and elimination. Reaction analyses make use of perceptual data including rings, functional groups, pK(,a)'s, nucleophiles and electrophiles. In addition, pedagogic rules for the correct manner in which to predict products for a reacting system have been developed.
Degree
Ph.D.
Subject Area
Organic chemistry
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