Chem 232 Lecture 12 - UIC Department of Chemistry - University of ...
Chem 232 Lecture 12 - UIC Department of Chemistry - University of ...
Chem 232 Lecture 12 - UIC Department of Chemistry - University of ...
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Regioselectivity - 2nd RationaleElectronic Effects Control Regioselectivity. . .both carbons in alkene develop partial positive charge in transition state; moresubstituted = more partially positively charged = hydride (H:) transfer preferred(faster) to that carbon atom.Lewis acidLewis baseπ-complexπ-complexmost substituted =most partially positively charged =most electrophilic carbon atom =want electrons from a nucleophile mostrearrangedπ-complex<strong>University</strong> <strong>of</strong> Illinois<strong>UIC</strong>at Chicago CHEM <strong>232</strong>, Spring 2010Slide 15<strong>Lecture</strong> <strong>12</strong>: February 1815
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