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http://hdl.handle.net/11375/20856
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DC Field | Value | Language |
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dc.contributor.advisor | Warkentin, John | - |
dc.contributor.author | Thorpe, James William | - |
dc.date.accessioned | 2016-11-30T15:47:09Z | - |
dc.date.available | 2016-11-30T15:47:09Z | - |
dc.date.issued | 1971-10 | - |
dc.identifier.uri | http://hdl.handle.net/11375/20856 | - |
dc.description.abstract | <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> | en_US |
dc.language.iso | en_US | en_US |
dc.subject | acetate, catalyzed, bromination, deuterium, bimolecular displacement, reactions | en_US |
dc.title | Acetate-Catalyzed Bromination and Deuterium Exchange of 2-Butanone (I). The Mechanism for the Bimolecular Displacement Reactions of α-Haloketones (II) | en_US |
dc.type | Thesis | en_US |
dc.contributor.department | Chemistry | en_US |
dc.description.degreetype | Thesis | en_US |
dc.description.degree | Doctor of Philosophy (PhD) | en_US |
Appears in Collections: | Digitized Open Access Dissertations and Theses |
Files in This Item:
File | Description | Size | Format | |
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Thorpe_James_W._1971Oct_Ph.D..pdf | 6.48 MB | Adobe PDF | View/Open |
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