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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 |
Files in This Item:
File | Description | Size | Format | |
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Tee_Oswald_S_196509_MSc.pdf | 4.44 MB | Adobe PDF | View/Open |
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