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

Slides:

Advertisements

Similar presentations

Aldehid dan Keton.

Advertisements

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

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

© 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.

12.5 The Acidity of an  -Hydrogens 1  -hydrogen -- ++ Main Menu  hydrogen of a carbonyl group is more acidity than a typical hydrogen in hydrocarbons.

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.

Carbon-Carbon Bond Forming Reactions. I. Substitution Reaction II. Addition Reaction.

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

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

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.

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

The Haloform Reaction Under basic conditions, halogenation of a methyl ketone often leads to carbon-carbon bond cleavage. Such cleavage is called the haloform.

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.

1 Enol & Enolate Condensations Chapter Enolate (nucleophilic) chemistry Made with 1 equivalent of base!!!! Not catalyst.

HCN and CN – in synthesis Increasing carbon chain length.

Hydrocarbons. Hydrocarbons Simplest organic compounds containing only carbon and hydrogen.

Aldehyde & Ketone.

CH 23: Carbonyl Condensation Reactions

Created by Professor William Tam & Dr. Phillis Chang Ch Chapter 18 Reactions at the  Carbon of Carbonyl Compounds Enols and Enolates.

Chapter 24 Carbonyl Condensation Reactions The Aldol Reaction In the aldol reaction, two molecules of an aldehyde or ketone react with each other.

Created by Professor William Tam & Dr. Phillis Chang Ch Chapter 18 Reactions at the  Carbon of Carbonyl Compounds Enols and Enolates.

Aldehydes, Ketones, Carboxylic Acids and Amides The carbonyl group >C=O is one of the most biologically important chemical entities in Organic Chemistry.

Carbonyl Alpha-Substitution Reactions

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

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

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

Please don’t do problem 31a, but please do problem 32c.

Examples: Aldehydes and ketones

Carbonyl Group (II) Aldehydes and Ketones Nanoplasmonic Research Group Organic Chemistry Chapter 9 Part II.

Reduction of Aldehydes and Ketones Complete reduction of a carbonyl group to a methylene (-CH 2 -) group is possible by two different methods 1)Wolff-Kishner.

Chapter 12: Alcohols from Carbonyl Compounds CH 12-1 Alcohol RedOx Oxidation (loss of H) of alcohols to form carbonyls Reduction (gain of H) of carbonyls.

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

1 Derivatives of Carboxylic Acids Lysergic acid diethylamide (LSD)

Chapter 22. Carbonyl Alpha-Substitution Reactions Based on McMurry’s Organic Chemistry, 6 th edition ©2003 Ronald Kluger Department of Chemistry University.

Oxidation-Reduction & Organometallic

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

Carbonyl compounds “Class I” “Class II”.

Chapter 22: Carbonyl Alpha-Substitution Reactions

Carbonyl compounds - reaction of the aldol type

Ch 17- Carboxylic Acids and their derivatives

a-Halogenation of Carboxylic Acids

Stabilized Carbanions with One -M (I)

Chapter 22 Carbonyl Alpha-Substitution Reactions

ENOLATE ANIONS AND ENAMINES

Another Equilibrium: Reaction At The a-Position

The halogens / Qualitative tests Module Enthalpy changes

Enol & Enolate Condensations

Organic Chemistry Reaction Scheme Acid + Base → Carboxylic salt + NH4+

Electron Distribution in Keto-Enol Tautomers

2.1 UNSATURATED HYDROCARBONS

CH 2-3 Survey of other Functional Groups in Organic Compounds

Organic Chemistry II Chapter 22 Carbonyl Alpha-Substitution Reactions

Extent of Enolization.

HCN and CN– in synthesis

CARBONYL CONDENSATION REACTION DEPARTMENT OF CHEMISTRY

REACTIONS OF GRIGNARD REAGENTS

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

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

Carbonyl Compounds III

Presentation transcript:

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

p. 696 I. Carbonyl  -Substitution using Enols 3. Limitations of Enols a. Equilibrium

p. 696 I. Carbonyl  -Substitution using Enols 3. Limitations of Enols a. Equilibrium b. Reactivity

p. 696 II. Carbonyl  -Substitution using Enolates 1. Advantages of Enolates a. Reactivity

Fig. 17-5, p. 703 Electron Distribution in Enolates Resonance Hybrid

p. 696 II. Carbonyl  -Substitution using Enolates 1. Advantages of Enolates a. Reactivity b. Quantitative formation

II. Carbonyl  -Substitution using Enolates 2. Preparation of Enolates a. pKa’s of important  -hydrogens

p. 696 II. Carbonyl  -Substitution using Enolates 2. Preparation of Enolates a. pKa’s of important  -hydrogens b. The Bases Used [6] Li + - CH 2 CH 2 CH 2 CH 3 CH 3 CH 2 CH 2 CH %

p. 696 II. Carbonyl  -Substitution using Enolates 3. Reactions of Enolates a. The reactive site

p. 696 II. Carbonyl  -Substitution using Enolates 3. Reactions of Enolates a. The reactive site b. Reactions of ketones i. thermodynamic and kinetic enolates.

p. 696 II. Carbonyl  -Substitution using Enolates 3. Reactions of Enolates a. The reactive site b. Reactions of ketones i. thermodynamic and kinetic enolates. c. Reactions of nitriles and esters

p. 696 II. Carbonyl  -Substitution using Enolates 3. Reactions of Enolates d. Active methylene compounds i. Malonic ester synthesis

p. 696 II. Carbonyl  -Substitution using Enolates 3. Reactions of Enolates d. Active methylene compounds ii. DAM amino acid synthesis