Chapter 19-1

Chapter 19-1 - CHEM 262 Wei You Chapter 19. Enolate Anions...

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11 CHEM 262 Wei You Chapter 19. Enolate Anions (1)
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Click to edit Master subtitle style The carbon adjacent to the carbonyl is designated as the α-carbon. Electrophilic substitution occurs at the α-position via one of two possible intermediates: General Overview: Enol vs. Enolate 22
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Click to edit Master subtitle style A carbonyl compound with a hydrogen on its α-carbon rapidly equilibrates with its enol tautomer Difference between Tautomers and Resonance Forms: Tautomers are structural isomers Resonance forms are representations of contributors to a single structure Difference between Tautomers and conventional structural isomers Tautomers interconvert rapidly while ordinary isomers do not. Keto-Enol Tautomerism 33
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Click to edit Master subtitle style Acid Catalysis of Enolization 1. proton addition 2. elimination 44
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Click to edit Master subtitle style 1. proton removal (elimination) 2. protonation to reform base and enol Base Catalysis of Enolization 55
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Click to edit Master subtitle style Enols behave as nucleophiles More electron rich than alkenes due to the electron donating OH group General Reactivity of Enols 66
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Reaction : α -Halogenation α -Halogenation: aldehydes and ketones with at least one α - hydrogen react at an α -carbon with Br2 and Cl2
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Chapter 19-1 - CHEM 262 Wei You Chapter 19. Enolate Anions...

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