Elementary Steps Associated with Addition and Elimination   Reactions
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The Organic and Macromolecular Chemistry Program supports the                   research of Drs. Heinz and Judith Koch, which aims at an                        experimental study of those electronic factors that influence                   1,2-elimination reactions.  The base induced elimination of a                   hydrogen and a leaving group (x) from an adjacent carbon is a                   very complicated process that has relevance to both biological                  and industrial chemistry.  The reverse process, the addition of                 HX across a double bond is also a major reaction in organic                     chemistry and an understanding of its various mechanisms is an                  important topic worthy of study.                                                                                                                                More specifically, proton-transfer reactions between carbon and                 oxygen will be studied and compared to ejection of halide from                  carbanion intermediates that are generated in alcoholic                         alkoxide solutions.  Reactions of saturated haloalkanes with                    alkoxide result in proton transfer from carbon to oxygen to                     form a hydrogen-bonded carbanion with a beta-halide.  The anion                 can be neutralized by either a loss of the beta-halide to form                  an alkene, or transfer of the proton back to carbon (internal                   return).  The latter is a no-reaction process, but it can be                    detected by the study of primary kinetic isotope effects of                     hydrogen associated with the elimination reaction.  A third                     reaction would lead to a new carbanion that is free of contact                  stabilization.  If that anion is neutralized prior to halide                    loss, the process can be detected by using a deuterated alcohol                 as solvent.  Both alpha and beta-carbon isotope effects                         associated with the eliminations will also be measured.                                                                                                         Reactions of fluorohaloalkenes with alkoxide generate a free                    carbanion directly.  If reaction occurs in alcohol there is a                   competition between loss of halide or protonation to neutralize                 the anion.  Chemistry of carbanions generated by both methods                   will be compared.
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[{'Code': '1938', 'Text': 'Chemical Instrumentation'}, {'Code': '1944', 'Text': 'BIMOLECULAR PROCESSES'}, {'Code': '9120', 'Text': 'CROSS-DIRECTORATE PROGRAMS'}]
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