Chemistry of Carbonyl Compounds (McM 19-12) Nucleophilic addition / substitution May also be acid cat.

Slides:

Advertisements

Similar presentations

Aldehydes, ketones. Required background: Structure of alkenes Nucleophilic substitution S N 1, S N 2 Essential for: 1. Carboxylic aids and their derivatives,

Advertisements

© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 19 Carbonyl Compounds III Reactions at the  -Carbon.

Organic Chemistry, 6th Edition L. G. Wade, Jr.

Condensations and Alpha Substitutions of Carbonyl Compounds

1 Nucleophilic reactions involving enolate anions Aldehydes, Ketons and other carbonyl compounds having H on α-C -> in equilibrium (in solution) -> Keto-Enol.

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.

Enolate Anions Chapter 19 Chapter 19.

Intermolecular a-alkylation and acetoacetic and malonic ester

Organic Chemistry 4 th Edition Paula Yurkanis Bruice Chapter 18 Carbonyl Compounds II Radicals Irene Lee Case Western Reserve University Cleveland, OH.

Chapter 23. Carbonyl Condensation Reactions

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.

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Modified slides of William Tam & Phillis Chang Ch Chapter 17 Carboxylic Acids and Their Derivatives NucleophilicAddition–Elimination at the Acyl.

© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 18 Carbonyl Compounds II Reactions of Aldehydes and Ketones.

Carbanions II Carbanions as nucleophiles in S N 2 reactions with alkyl halides. a) Malonate synthesis of carboxylic acids b) Acetoacetate synthesis of.

Carbanions | — C: – | The conjugate bases of weak acids, strong bases, excellent nucleophiles.

1 Nucleophilic reactions involving enolate anions (2) Aldehydes, Ketons and other carbonyl compounds having H on α-C -> in equilibrium (in solution) ->

Keto-enol tautomerization enolization “normal” aldehydes and ketones K eq = ~

Carbonyl Compounds III

Chapter 19 Enolates and Enamines.

Aldehydes and Ketones  Nomenclature  Properties  Preparation reactions of Aldehydes and Ketones  Characteristic reactions of Aldehydes and Ketones.

Reactions for Exam (you will have the reducing agent chart on exam): Everything from 241a (epoxidations, halides from alcohols, ether synthesis) Electrophilic.

OrgChem- Chap20 1 Chapter 20 Enolates / Other Carbon Nucleophiles C-C bond formation is very important  larger, more complex organic molecule can be made.

CARBONYL CONDENSATION REACTIONS

John E. McMurry Paul D. Adams University of Arkansas Nucleophilic Acyl Substitution Reactions.

Chapter 23. Carbonyl Condensation Reactions

Chapter 23. Carbonyl Condensation Reactions

WWU -- Chemistry Reactions of  Hydrogens: Condensation Reactions Chapter 21 These images should be printed in color, if possible, otherwise the images.

© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 18 Carbonyl Compounds II Reactions of Aldehydes and Ketones.

John E. McMurry Paul D. Adams University of Arkansas Chapter 23 Carbonyl Condensation Reactions.

CH 23: Carbonyl Condensation Reactions

Carboxylic Acids Derivatives other than Ester Nanoplasmonic Research Group Organic Chemistry Chapter 10 Part II.

Chapter 23. Carbonyl Condensation Reactions

Dr. Hayder kh. Q. Ali School of Bioprocess Engineer UniMAP.

23.7 The Claisen Condensation Reaction

Carbonyl Condensation Reactions

Chem 341 Review for Finals Structure Determination NMR –Chemical shifts, splitting patterns, integrations IR –ROH, C=O Formula => # of Rings + Pi-Bonds.

P. 696 I. Carbonyl  -Substitution using Enols 2. Reactions of Enols c.  -Halogenation of aldehydes and ketones d. The Hell-Volhard-Zolinskii reaction.

Introduction b-Dicarbonyl compounds have two carbonyl groups separated by a carbon Protons on the a-carbon of b-dicarbonyl compounds are acidic (pKa =

1 Carbonyl Condensation Reactions Carbonyl compounds are both the electrophile and nucleophile in carbonyl condensation reactions.

Properties of ,  -Unsaturated Aldehydes and Ketones 18-8 Conjugated unsaturated aldehydes and ketones are more stable than their unconjugated isomers.

Enols and Enolates  Substitutions and Condensations of Ketones and Aldehydes.

WWU -- Chemistry The Claisen Ester Condensation Taken from: 1c.ppt 1c.ppt.

126 Chapter 18: Enols and Enolates 18.1: The  -Carbon Atom and its pK a.

Chapter 17 Aldehydes and Ketones II. Aldol Reactions

Examples: Aldehydes and ketones

John E. McMurry Paul D. Adams University of Arkansas PREVIEW TO CARBONYL CHEMISTRY.

© 2014 Pearson Education, Inc. Chad Snyder, PhD Grace College Chapter 22 Lecture Organic Chemistry, 9 th Edition L. G. Wade, Jr. Condensations and Alpha.

Alpha Carbon Chemistry: Enols and Enolates

Carbanions | — C: – The conjugate bases of weak acids,

Addition and Condensation reactions of

Ch 17- Carboxylic Acids and their derivatives

Objectives for Chapter 23

Chapter 23 Carbonyl Condensation Reactions

Chapter 20 Enolates / other Carbanions

Alpha Carbon Chemistry: Enols and Enolates

Alpha Carbon Chemistry: Enols and Enolates

Chapter 23. Carbonyl Condensation Reactions

Alpha Carbon Chemistry: Enols and Enolates

ENOLATE ANIONS AND ENAMINES

Properties Nomenclature Preparation Reactions Synthesis

Another Equilibrium: Reaction At The a-Position

Extent of Enolization.

Chapter 23 Carbonyl Condensation Reactions

Alpha Substitution Alpha substitution is the substitution of one of the hydrogens attached to the a carbon for an electrophile. The reaction occurs through.

Chapter 23 Substitution Reactions of Carbonyl Compounds

Qualitative Iodoform Test

TOPIC 6: ALDOL REACTIONS AND THE SYNTHESIS AND REACTIONS OF b-DICARBONYL COMPOUNDS (Chapters 17 and 19)

of carbonyl group chemistry

Presentation transcript:

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)