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Please use this identifier to cite or link to this item: http://hdl.handle.net/11375/31664
Title: THE RELATIVE RATES OF BΛSE-CATALYSED HYDROGEN-DEUTERIUM EXCHANGE IN METHYL ETHYL KETONE
Other Titles: BASE-CATALYZED HYDROGEN-DEUTERIUM EXCHANGE OF A SIMPLE KETONE
Authors: Tee, Oswald Sydney
Advisor: Warkentin, J.
Department: Chemistry
Keywords: Relative rates;Hydrogen;Deuterium;Methyl Ethyl Ketone;Enolization;N.M.R. spectroscopy
Publication Date: Sep-1965
Abstract: The relative rates of hydrogen deuterium exchange at the α- and α' -positions in the simplest unsymmetrical ketone were determined by use of N.M.R. spectroscopy. It has been long held that in base-catalysed enolization processes the least alkyl substituted opposition is cost reactive. However it was observed that in the exchange reaction of 2-butanone catalyzed by OD- in D2O, the α- and α'-positions are similarly reactive while for weaker bases (p-NO2PHO-, AcO- ) the cost substituted α- position is the more reactive. The results are discussed in terms of a model for the transition state for enolization, and a continuity of mechanism between the acid-catalyzed, and base-catalyzed processes is proposed.
URI: http://hdl.handle.net/11375/31664
Appears in Collections:Digitized Open Access Dissertations and Theses

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