<p> The regioselectivities of bromination and deuterium exchange of 2-butanone are shown to be the same, under identical conditions. This work firmly establishes that enolization is the rate-determining step for the former reaction, contrary to some recent reports in the literature.</p> <p> The steric effects and activation parameters in the bimolecular nucleophilic displacement reactions of a series of α-haloketones and alkyl halides are shown to be inconsistent with either a bridging or conjugation mechanism for the observed rate
enhancements of haloketone over alkyl halide.</p> <p> The stereoelectronic requirements of this mechanism are tested in a system where the stereochemistry is known (cis- and
trans-chlorocyclohexanones). The activation parameters suggest that only in the case where the geometry is correct for maximum conjugation (trans-chlorocyclohexanone) is there an appreciable difference in mechanism (stereoelectronically) from displacement at ordinary saturated carbon.</p> / Thesis / Doctor of Philosophy (PhD)
| Identifer | oai:union.ndltd.org:mcmaster.ca/oai:macsphere.mcmaster.ca:11375/20856 |
| Date | 10 1900 |
| Creators | Thorpe, James William |
| Contributors | Warkentin, John, Chemistry |
| Source Sets | McMaster University |
| Language | en_US |
| Detected Language | English |
| Type | Thesis |
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