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Chemistry of Carbonyl Compounds (McM 19-12) Nucleophilic addition / substitution May also be acid cat.
The Cannizzarro reaction (McM 19.13) Hydride as leaving group!
Conjugate Addition (McM 19.14) 1,2-addition, Ex: Alchohols Organolithium 1,4-addition, Ex: Amines Organocuprates Michael reaction (McM 23.11) Michael acceptor
Robinson Annulation (McM 23.13) Ring forming react. annulus (lat.) = ring
E:- Alkyl halides - Carbonyl compounds (Aldol, Claissen condens.) - Halides
Michael acceptor Enolizable Alkylation of enolate anions (McM 22.8) Ketones, esters, nitriles (Aldehydes: condensation) Base: Strong, sterical hindrance
Alkylation of 1,3-dicarbonyl compounds followed by decarboxylation
Enamines as enolate equivalents (McM 23.12, Lab ex. 11) Synthesis of enamines (cf McM 19.9)
Reactivity of enamines Alkylation (alkyl halides) Conjugate addition (Michael acceptors) Acylation (acid halides) Monoalkylation No strong base
Halogenation of enolate anions (McM 22.7)
Halogenation of neutral enols (McM 22.3) mainly monohalogenated prod. -Bromination of acids (McM 22.4)
Carbonyl condensations in nature (McM 21.8, 23.14) Acetyl-CoA (Acetyl co-enzyme A) Synthesis of Acetylcholine (neurotransmittor) Acyl-CoA
Polyesters, polyamides etc (McM 21.9) Acyl subst react Step-Growth polymers (Chain-Growth polymers: Polyenes)
OrgChem- Chap20 1 Chapter 20 Enolates / Other Carbon Nucleophiles C-C bond formation is very important larger, more complex organic molecule can be made.
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 19 Carbonyl Compounds III Reactions at the -Carbon.
Enols and Enolates Substitutions and Condensations of Ketones and Aldehydes.
Keto-enol tautomerization enolization “normal” aldehydes and ketones K eq = ~
Chapter 23. Carbonyl Condensation Reactions Based on McMurry’s Organic Chemistry, 6 th edition.
Organic Chemistry 4 th Edition Paula Yurkanis Bruice Chapter 19 Carbonyl Compounds III Reactions at the -Carbon Irene Lee Case Western Reserve University.
Chapter 22 Alpha Substitution and Condensations of Enols and Enolate Ions Jo Blackburn Richland College, Dallas, TX Dallas County Community College District.
Chapter 13 Substitution Alpha to Carbonyl Groups Formation and Reactions of Enolate Anions and Enols Alkylation of Ketones and Esters: S N 2 Reaction with.
191 Chapter 21: Ester Enolates 21.1: Ester Hydrogens and Their pK a ’s. The -protons of esters are less acidic that ketones and aldehydes. Typical.
Chapter 23. Carbonyl Condensation Reactions Based on McMurry’s Organic Chemistry, 7 th edition.
1 Nucleophilic reactions involving enolate anions Aldehydes, Ketons and other carbonyl compounds having H on α-C -> in equilibrium (in solution) -> Keto-Enol.
Chapter 23. Carbonyl Condensation Reactions Why this Chapter? Carbonyl condensation reactions also occur often in metabolic pathways. Also one of the general.
John E. McMurry Paul D. Adams University of Arkansas Chapter 23 Carbonyl Condensation Reactions.
CH 23: Carbonyl Condensation Reactions Renee Y. Becker CHM 2211 Valencia Community College.
189 Chapter 20: Enols and Enolates 20.1: Aldehyde, Ketone, and Ester Enolates.
Dr. Hayder kh. Q. Ali School of Bioprocess Engineer UniMAP.
1 Examples: Aldehydes and ketones. 2 Conditions for Alpha Substitution Add quickly.
CONDENSATION CARBONYL CONDENSATION REACTIONS. CARBONYL CONDENSATION REACTIONS Aldol Reaction Dehydration of Aldol Products Intramolecular Aldol Reaction.
Aldehydes, ketones. Required background: Structure of alkenes Nucleophilic substitution S N 1, S N 2 Essential for: 1. Carboxylic aids and their derivatives,
1 Carbonyl Condensation Reactions Carbonyl compounds are both the electrophile and nucleophile in carbonyl condensation reactions.
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 18 Carbonyl Compounds II Reactions of Aldehydes and Ketones.
WWU -- Chemistry The Claisen Ester Condensation Taken from: 1c.ppt 1c.ppt.
Carbanions II Carbanions as nucleophiles in S N 2 reactions with alkyl halides. a) Malonate synthesis of carboxylic acids b) Acetoacetate synthesis of.
Chapter 19 Synthesis and Reactions of -Dicarbonyl Compounds: More Chemistry of Enolate Anions.
WWU -- Chemistry Reactions of Hydrogens: Condensation Reactions Chapter 21 These images should be printed in color, if possible, otherwise the images.
Properties of , -Unsaturated Aldehydes and Ketones 18-8 Conjugated unsaturated aldehydes and ketones are more stable than their unconjugated isomers.
1 Nucleophilic reactions involving enolate anions (2) Aldehydes, Ketons and other carbonyl compounds having H on α-C -> in equilibrium (in solution) ->
John E. McMurry Paul D. Adams University of Arkansas PREVIEW TO CARBONYL CHEMISTRY.
126 Chapter 18: Enols and Enolates 18.1: The -Carbon Atom and its pK a.
Created by Professor William Tam & Dr. Phillis Chang Ch Chapter 19 Condensation and Conjugate Addition Reactions of Carbonyl Compounds More Chemistry.
CHE2202, Chapter 23 Learn, 1 Carbonyl Condensation Reactions Chapter 23 Suggested Problems – 1-22,27-31,41,48-9,58,
19-1 Enolate Anions Chapter Reactions of Chapter 19 Aldol reaction (aldehyde or ketone) Crossed Aldol Intramolecular Aldol (cyclic) Claisen.
P. 696 I. Carbonyl -Substitution using Enols 2. Reactions of Enols c. -Halogenation of aldehydes and ketones d. The Hell-Volhard-Zolinskii reaction.
Carboxylic Acids Derivatives other than Ester Nanoplasmonic Research Group Organic Chemistry Chapter 10 Part II.
Organic Chemistry 4 th Edition Paula Yurkanis Bruice Chapter 18 Carbonyl Compounds II Radicals Irene Lee Case Western Reserve University Cleveland, OH.
Aldehydes and Ketones Nomenclature Properties Preparation reactions of Aldehydes and Ketones Characteristic reactions of Aldehydes and Ketones.
Carbanions | — C: – | The conjugate bases of weak acids, strong bases, excellent nucleophiles.
Chapter 17 Aldehydes and Ketones II. Aldol Reactions.
19-1 Chapter 19 Enolates and Enamines Formation of an Enolate Anion Enolate anions are formed by treating an aldehyde, ketone, or ester, which.
Reactions for Exam (you will have the reducing agent chart on exam): Everything from 241a (epoxidations, halides from alcohols, ether synthesis) Electrophilic.
John E. McMurry Paul D. Adams University of Arkansas Nucleophilic Acyl Substitution Reactions.
Chem 341 Review for Finals Structure Determination NMR –Chemical shifts, splitting patterns, integrations IR –ROH, C=O Formula => # of Rings + Pi-Bonds.
Modified slides of William Tam & Phillis Chang Ch Chapter 17 Carboxylic Acids and Their Derivatives NucleophilicAddition–Elimination at the Acyl.
Reaction of an ester having an hydrogen with 1 equivalent of a base to yield a -keto ester 23.7 The Claisen Condensation Reaction.
Chapter 22 Copyright © 2010 Pearson Education, Inc. Organic Chemistry, 7 th Edition L. G. Wade, Jr. Condensations and Alpha Substitutions of Carbonyl Compounds.
A library of the enol and enolate mediated carbonyl compound reactions: Intermolecular -alkylation and acetoacetic and malonic ester synthesis via enolate.
© 2014 Pearson Education, Inc. Chad Snyder, PhD Grace College Chapter 22 Lecture Organic Chemistry, 9 th Edition L. G. Wade, Jr. Condensations and Alpha.
Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to the Carbonyl Group.
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