有機化學第23ç« ï&f

有機化學第23ç« ï&f

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2009/6/11 1 Chapter 23. Carbonyl Condensation Reactions + H 2 O Electrophile Nucleophilie Based on McMurry’s Organic Chemistry , 7 th edition A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule. Carbonyl Group as an Electrophile Nucleophlic Addition (Chapter 19) Nucleophilic Acyl Substitution (Chapter 21 Electrophile 2 Nucleophilic Acyl Substitution (Chapter 21)
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2009/6/11 2 Enolate Ion or Enol as a Nucleophilie Alpha Substitution (Chapter 22) Nucleophilie 3 Reaction of Carbonyl Group Carbonyl Condensation (Chapter 23) Electrophile Nucleophilie Carbonyl compounds are both the electrophile and nucleophile in carbonyl 4 in carbonyl condensation reactions
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2009/6/11 3 Why this Chapter? Carbonyl condensation reactions also occur often in metabolic pathways. Also one the general methods used to form C-C bonds. 5 + H 2 O OUTLINE ± Condensations of Aldehydes and Ketones: The Aldol Reaction ± Carbonyl Condensation Reactions versus Alpha-Substitution Reactions 6 ± Dehydration of Aldol Products: Synthesis of Enones ± Using Aldol Reactions in Synthesis ± Mixed Aldol Reactions ± Intramolecular Aldol Reactions
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2009/6/11 4 OUTLINE ± The Claisen Condensation Reaction ± Mixed Claisen Condensations ± Intramolecular Claisen Condensations: The Dieckmann Cyclization ± Conjugated Carbonyl Additions: The Michael Reaction 7 ± Carbonyl Condensations with Enamines: The Stork Enamine Reaction ± The Robinson Annulation Reaction ± Biological Carbonyl Condensation Reactions 23.1 Carbonyl Condensation: The Aldol Reaction Mechanism of Carbonyl Condensation Reactions Carbonyl condensation reactions utilize α -substitution steps 8
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2009/6/11 5 Nucleophilie Electrophile 9 The Aldol Reaction Acetaldehyde reacts in basic solution (NaOEt, NaOH) with another molecule of acetaldhyde The β -hydroxy aldehyde product is aldol ( ald ehyde + alcoh ol ) This is a general reaction of aldehydes and ketones 10
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2009/6/11 6 The Equilibrium of the Aldol The aldol reaction is reversible, favoring the condensation product only for aldehydes with no α substituent RCH 2 CHO Steric factors are increased in the aldol produc 11 Steric factors are increased in the aldol product enolate ion Mechanism 12
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2009/6/11 7 W.E. 23.1 13 P. 23.1 14
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2009/6/11 8 P. 23.1 15 P. 23.1 16
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This note was uploaded on 11/11/2010 for the course CHE CH2005 taught by Professor 曹恒光 during the Spring '10 term at National Central University.

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有機化學第23ç« ï&f

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