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Published byDelilah Robinson Modified over 9 years ago
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Enols and Enolates Substitutions and Condensations of Ketones and Aldehydes
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Tautomerization Accelerated in Acid
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-Halogenation
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Reaction Occurs via Enol
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Tautomerization Acceleration in Base
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Alkylation in Base Reaction with 1 o RX
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Using LDA as Base to form Enolate
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Alkylation to C=O C-alkylation preferred
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Alkylation Occurs on Less Hindered Side of C=O
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Malonic Ester Synthesis of Carboxylic Acids
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H’s are unusually acidic
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Decarboxylation (loss of CO 2 )
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2 Acidic H’s, 2 Alkylations; Determine the Product of the Synthesis
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All -keto acids are unstable and Decarboxylate
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Enamines can be Alkylated
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Alkylation of an Enamine Position is Activated
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Complements LDA Reaction
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LDA vs. Enamine Reaction
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Selenation: Formation of -Unsaturated Ketones
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Mechanism
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Synthesis
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Aldol Condensation
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Enolate Undergoes Nucleophilic Addition
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Aldol Condensation Dimerization of 3-Pentanone
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Crossed Aldol Between 2 Different C=O Compounds
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Four Possible Condensation Products
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Crossed Aldol Condensation
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Dehydration of Aldol Products
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Predicting Aldol Dehydration Products
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Intramolecular Aldol
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Predict the Product
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Conjugate Addition
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1,2 - vs. 1,4 - Addition
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Michael Addition Conjugate Addition of Enolate to - Unsaturated Ketone
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Robinson Annulation: Michael Addition followed by Aldol Consensation
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