Author

Mike Bauman

Document Type

Thesis - Open Access

Award Date

1978

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

William Wadsworth, Jr.

Abstract

From these results the following conclusions may be drawn: 1. The stereochemistry of nucleophilic substitution at phosphorus is influenced by the basicity of the leaving group with the more basic leaving group favoring retention. 2. Lithium ion diverts the reaction to retention by forming an intimate ion-pair with the nucleophile which then attacks phosphorus. This associated ion is less reactive than the unassociated nucleophile. 3. For the retention mechanism the leaving group participates in the rate determining step. 4. The mechanism for retention entails a more sterically unfavorable configuration than for inversion.

Library of Congress Subject Headings

Substitution reactions
Esters
Organophosphorus compounds

Format

application/pdf

Publisher

South Dakota State University

Included in

Chemistry Commons

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