Orgo II - Week 11 (Montague-Smith Fall 2015)
Orgo II - Week 11 (Montague-Smith Fall 2015) CHEM241
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This 14 page Class Notes was uploaded by Carianne Powers on Sunday November 29, 2015. The Class Notes belongs to CHEM241 at University of Maryland taught by Dr. Montague-Smith in Summer 2015. Since its upload, it has received 30 views. For similar materials see Organic Chemistry 2 in Chemistry at University of Maryland.
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Date Created: 11/29/15
November 10 Will not be on an exam Gilman Reagent R' adds twice Gilman is the least reactive reagent. It can't react with the ketone. Don't worry about anhydrides or thioesters. Don't worry about amides. Enols, Enolates, and Carbonyl Condensations Chapter 22 Beta proton pKa ~45 Aldehydes/ketones ~15-20 Esters ~25 Alpha proton pKa depends Nitriles ~25 Alpha protons are significantly more acidic than beta protons. November 12 Base: "Enol-Keto Tautamerization" Two isomers in rapid equilibrium In both acidic and basic conditions, that alpha carbon can act as a nucleophile. Acid: *keep track of the correct number of carbons Base: *stereochem won't be present on exams Acid: Stop after one addition of Bromine, even with excess available Why only once? Never good to have a charge next to a partial charge If we happen to have a good nucleophile ...you can do an hanging around... SN2 rather easily THE ALDOL CONDENSATION Aldol Addition