<p> The acetate-catalyzed bromination of acetone is shown to occur by an enolization mechanism, although the reactions involved in this process are more complex than
has been supposed.</p> <p> A study of the activation parameters for the enolization
of some bromoacetones, and an observed linear free energy relationship between enolization rate constants, and acid ionization constants, shows that the transition state for this process resembles enolate and not enol.</p> <p> Bromine substitution in ketones accelerates enolization rates on both sides of the carbonyl group.</p> <p> The acetate-catalyzed enolization of 2-butanone favours the methylene group by a factor of nearly two.
This fact is interpreted in terms of methyl groups being inductively electron-withdrawing in their effect in forming an enolate transition state.</p> / Thesis / Doctor of Philosophy (PhD)
| Identifer | oai:union.ndltd.org:mcmaster.ca/oai:macsphere.mcmaster.ca:11375/17545 |
| Date | 10 1900 |
| Creators | Cox, Robin Anthony |
| Contributors | Warkentin, J., Chemistry |
| Source Sets | McMaster University |
| Language | en_US |
| Detected Language | English |
| Type | Thesis |
Page generated in 0.0018 seconds