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Reactions of Enolate Anions: Enolates + Electrophiles II Condensations: Many Types, and (Other Reactions) Condensations: Aldol, Claisen, Dieckmann, Acetoacetic ...
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Halogenation and Enolate Formation. Halogenation of ... Enamines behave like Enolates. Enamines stop at one addition. Single Addition makes Enamines useful ...
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Michael addition ( , -unsaturated carbonyl) Robinson Annulation (cyclic from Michael aldol) ... Enamines The Stork Reaction ...
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A proton on the carbon flanked by the two carbonyl groups is ... Keto esters are made by the reaction shown, which is called the ... (barbital; Veronal) ...
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Chapter 21: Ester Enolates
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Alkylation of Enolate Ions The malonic ester synthesis The acetoacetic ester synthesis Direct alkylation of ketones, esters and nitriles Relative acidity of selected ...
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Chapter 18: Enols and Enolates
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In most cases the keto form is favored at equilibrium. 99.98% 0.02% 2. Acid-Catalyzed Process ... Usually, the initially-formed -hydroxyketone dehydrates to ...
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Chiral Lewis Acids for Asymmetric Aldol Reactions. Chiral Lewis Acids for Asymmetric Aldol Reactions. The Extension to Allylation Reactions ...
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Carbonyl compounds like aldehydes, ketones and esters can also be ... 11. Stork Enamine Reactions: Use of enamines as enol equivalents. imine. enamine. 10 amine ...
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no involvement of halogen until after the. rate-determining step ... second stage is reaction of enol with halogen; is faster than the first stage ...
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Other carbons are designated , , , etc. on the basis of their position with ... reaction because chloroform, bromoform, or iodoform is one of the products. ...
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a substituted acetoacetic ester. a substituted acetone ... Direct alkylation of ketones, esters, and nitriles (but NOT aldehydes) ...
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Title: CNChapter 22CTCarbonyl Alpha-Substitution Reactions Author: Ronald Kluger Last modified by: ChemStudent Created Date: 3/27/2003 10:05:42 PM
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Nucleophilic reactions involving enolate anions Aldehydes, Ketons and other carbonyl compounds having H on -C - in equilibrium (in solution) - Keto-Enol ...
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BASE CATALYZED DEPROTONATION TO FORM AN ENOLATE. Base removes a-hydrogen ... a-Carbanion in resonance with Enolate anion. Nucleophilic site ...
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Richland College, Dallas, TX. Dallas County Community College District ... Stork Reaction. Milder alkylation method than using LDA. Ketone 2 amine enamine. ...
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Enols and Enolates a Substitutions and Condensations of Ketones and Aldehydes Tautomerization Accelerated in Acid Reaction Occurs via Enol ...
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110. Reactions Initiated by Hydrometalations. An enolate. Compare with lithium enolate! ... 142. Reactions of Vinyl Halides. 143. The End ...
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Enolates and Enamines Enamines Acylation at a position Enamines undergo acylation when treated with acid chlorides and acid anhydrides. Could this be made via a ...
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Synthetic Applications of Enamines (p.960). Recall that the ... Enamines are reactive equivalents of enols and enolates and ... Type II Aldolase uses enamine chemistry ...
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Enolate Chemistry and Malonic Ester Synthesis ... Synthetic Polymers (less reactive esters and amides) Predicting Products Problems ...
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Claisen Ester Condensation (Intermolecular) and Dieckmann Cyclization ... Reaction Involving An Ester Enolate (Nucleophile) and An Ester (Electrophile) ...
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An enolate ion adds as a nucleophile to the electrophilic acceptor ... Immediate addition of an alkyl halide to completes the alkylation reaction ...
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Alkylation of (nucleophilic) Enolate Anions (Specific Example) ... anion. a carbonyl. compound. C9. Alpha, Beta-Unsaturated Carbonyl Compounds. C10 ...
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A carbon acid is a compound with a relatively acidic. hydrogen ... The Stork Enamine Reaction. Enamines are used in place of enolates in Michael. reactions ...
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Carbon is more electronegative than hydrogen. Bond Dipole moment points toward carbon ... Example: acetate anion, carbonate anion, enolate anion. Chapter 2 - Alkanes ...
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Erythro and Threo. Terms used for diastereomers with two adjacent ... Chain Lengthening. Epimerization. In base, H on C2 may be removed to form enolate ion. ...
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Electrophilic substitution occurs at this position through either an enol or enolate ion ... The enol then can react with another electrophile ...
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Asymmetric Enantioselective Ireland-Claisen Rearrangement using a Chiral Boron Reagent ... of the intermediate boron enolate: E/E educts afford the threo (syn) ...
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The nucleophilic carbon can react with an electrophile to form a new bond to carbon. ... Enolates are nucleophiles that react with a variety of electrophiles. ...
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... compounds are both the electrophile and nucleophile in carbonyl condensation reactions ... carbonyl compound to enolate form so it is not an electrophile ...
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NAMED REACTION IN ORGANIC CHEMISTRY
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Title: Project Overview Author: USER Created Date: 11/7/2001 3:36:02 PM Document presentation format: On-screen Show Company: USER Other titles
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Isocomene 2. !,3-dicarbonyl compounds and enol ethers 1. LDA - lithium diisopropylamide 2. !,3-dicarbonyl compounds and enol ethers 1.
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Organic Chemistry William H. Brown & Christopher S. Foote
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Rainer Ludwig Claisen (1851-1930) Developed the Claisen Condensation in 1887 What are the building blocks? sp2 orbitals p orbitals bond sp3 orbitals ...
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Stork Enamine Reaction. Robinson Annulation Reaction. General Mechanism of ... net effect of Stork Enamine reaction sequence is the Michael addition of a ...
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A. Initial Discoveries. B. Palladium Catalyzed Arylation of Diphenylsilyl Enol Ethers ... Initial Discoveries. 31. Plausible Mechanism for the Pd-Catalyzed ...
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B. Keto-enol tautomerism. 1. base catalyzed. keto. Chapter 22. 5. 2. acid ... 3. racemization: keto-enol tautomerism in action. Chapter 22. 7. Chapter 22. 8 ...
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ol. H3O - H2O. a,b-unsaturated aldehyde. aldols easily lose. water to form a. double bond ... Density - LUMO plots ( color scale 0.000 to 0.030 ) MORE ...
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Most aldehydes and ketones exist primarily in the keto form because of the ... An optically active aldehyde or ketone with a stereocenter at the a-carbon can ...
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Electrophiles. Nucleophiles. Stereochemistry/Asymmetric Variations. Historical ... Electrophile. Nucleophile. Hudlicky et al., J. Org. Chem. 1985, 50, 4300-4306 ...
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Chemistry of Carbonyl Compounds (McM 19-12) Nucleophilic addition ... Acetyl-CoA (Acetyl co-enzyme A) Synthesis of Acetylcholine (neurotransmittor) Acyl-CoA ...
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proposed. step 1: radical anion! or . anion radical! .unpaired spin and negative ... however, radical anions have never been detected by ESR spectroscopy in ...
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Mono ... de Hidrogenos en a en Compuestos Mono- y Di-Activados. 4. pKa de algunos ... Generalmente el equilibrio est desplazado hacia la forma ceto. 8 ...
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Sneak Peek: Keto-Enol Tautomerism. Reactivity of Enols: Mech. of Alpha-Substitution Rxns. ... Alpha Halogenation of Aldehydes and Ketones. Alpha ...
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Carbonyl compounds are both the electrophile and nucleophile in carbonyl condensation reactions ... 23.12 The Stork Enamine Reaction ...
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Sufixes Tet, Trig and Dig indicate the geometry of the carbon undergoing the RC. ... 3 to 7-exo-Trig are all favoured processes ...
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B. Dehydration of the Aldol Product. Aldol addition product readily loses H2O: 2-butenal. Dehydration is unavoidable when the product is highly conjugated. 5 ...
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Electrophilic Alkenes. Termite Self-Defense! 18.12. Conjugate Addition to ... Robinson Annelation - The Big Picture. 18.14. Conjugate Addition of Organocopper Reagents ...
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a-carbon containing acidic a-protons (the subject of this chapter) ... The amine is removed from the alkylated product by acid to give the alkylated ...
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Reaction to construct a new carbon-carbon bond. ... lewis acid and a lithium binaphthoxide moiety which serves as a Bronsted base. ...
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Experiment 22: THE SOLVENTLESS ALDOL-TYPE CONDENSATION Objectives: To synthesize an a,b unsaturated ketone from an aldehyde and a ketone using solvent-free conditions.
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Note the points at which amino acids. may enter the citric acid cycle. ... Another connection to amino acid metabolism. The Aspartate Malate Shunt ...
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