Date of Award
Bachelor of Science
Harry F. Herbrandson
Depending upon the halogenating agent and the reaction conditions d-ethyl medelate may form either d - or 1-ethyl phenylchloroacetate. Situations of this type are common and have proven to be an interesting and a productive field for investigation into the mechanisms of organic substitution reactions. The inversion reaction (Walden Inversion) appears to be the more typical of the two and is also the more readily explained. A and B ions have a repulsive effect upon each other and classical theory would demand that the ion B enter the molecule on the side opposite A. This displacement would of necessity result in an inversion of configuration. The hypothesis that this simple type of substitution always involves an inversion has been substantiated by a good deal of theoretical and experimental work. Substitutions which involve a retention of configuration must involve a fundamentally different mechanism. A frontal attack by the displacing ion would not seem feasible. A hypothesis that these reactions involve the formation of an intermediate and subsequent intramolecular decomposition has received support.
Mattson, Victor Frank, "Kinetics of Displacement Reactions Which Result in a Retention of Configuration" (1949). Honors Theses. 1970.