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

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.
Condensations and Alpha Substitutions of Carbonyl Compounds
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.
Reactions of Enols and Enolates. Ketones and aldehydes are in equilibrium with a small amount of the corresponding enol. This can be problematic, if one.
Intermolecular a-alkylation and acetoacetic and malonic ester

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.
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 = ~
Α,β-Unsaturated Carbonyl Compounds. α,β-Unsaturated Carbonyl Compounds, reactions: 1.electrophilic addition deactivated 2.nucleophilic addition activated.
Carbonyl Compounds III
Chapter 19 Enolates and Enamines.
Alkylation of Aldehydes and Ketones 18-4 Alkylation of enolates can be difficult to control. The alkylation of an aldehyde or ketone enolate is an example.
OrgChem- Chap20 1 Chapter 20 Enolates / Other Carbon Nucleophiles C-C bond formation is very important  larger, more complex organic molecule can be made.
Chapter 13: Aldehydes and Ketones
Carbonyl Compounds III: Chapter 13
CARBONYL CONDENSATION REACTIONS
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
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.
John E. McMurry Paul D. Adams University of Arkansas Chapter 23 Carbonyl Condensation Reactions.
WWU -- Chemistry Reactions of  Hydrogens: Condensation Reactions Chapter 21.
Aldehyde & Ketone.
CH 23: Carbonyl Condensation Reactions
Chapter 24 Carbonyl Condensation Reactions The Aldol Reaction In the aldol reaction, two molecules of an aldehyde or ketone react with each other.
Chapter 23. Carbonyl Condensation Reactions
Dr. Hayder kh. Q. Ali School of Bioprocess Engineer UniMAP.
Carbonyl Alpha-Substitution Reactions
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.
126 Chapter 18: Enols and Enolates 18.1: The  -Carbon Atom and its pK a.
18.11 Effects of Conjugation in  -Unsaturated Aldehydes and Ketones.
Chapter 17 Aldehydes and Ketones II. Aldol Reactions
Examples: Aldehydes and ketones
Carbonyl Group (II) Aldehydes and Ketones Nanoplasmonic Research Group Organic Chemistry Chapter 9 Part II.
Chapter 16 Aldehydes and Ketones I
© 2014 Pearson Education, Inc. Chad Snyder, PhD Grace College Chapter 22 Lecture Organic Chemistry, 9 th Edition L. G. Wade, Jr. Condensations and Alpha.
Carbanions | — C: – The conjugate bases of weak acids,
Addition and Condensation reactions of
Objectives for Chapter 23
Lecture 33 – Chapter 20 : Ester Hydrolysis
Chapter 20 Enolates / other Carbanions
Reactions of Enolate Anions: Enolates + Electrophiles II
Stabilized Carbanions with One -M (I)
Chapter 18 Enols and Enolates
CARBONYL CONDENSATION REACTION DEPARTMENT OF CHEMISTRY
Chapter 23. Carbonyl Condensation Reactions
Chapter 17 Carbonyl Alpha-Substitution and Condensation Reactions
ENOLATE ANIONS AND ENAMINES
CH 12-3: Grignard Reaction-I
Another Equilibrium: Reaction At The a-Position
CARBONYL COMPOUNDS ALDOL CONDENSATION
Dr. Pandit Khakre Asst. Prof Mrs. K.S.K. College, Beed.
Chapter 13 Reactions at the α-Carbon of Carbonyl Compounds
CARBONYL CONDENSATION REACTION DEPARTMENT OF CHEMISTRY
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
Aldol reactions.
Qualitative Iodoform Test
Presentation transcript:

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

2 Nucleophilic reactions involving enolate anions

3

4 Enolate anion Conjugated base

5 Nucleophilic reactions involving enolate anions Hydrogen Exchange Racemization

6 Nucleophilic reactions involving enolate anions Conjugation Enol-Form -> Keto-Form Progesterone (female sex hormone)

7 Nucleophilic reactions involving enolate anions Halogenation

8 Nucleophilic reactions involving enolate anions Alkylation of enolate anion Enolate anion acting as carbanion nucleophiles in S N 2 reaction

9 Nucleophilic reactions involving enolate anions Alkylation of enolate anion Reaction not possible with aryl halides

10 Nucleophilic reactions involving enolate anions Alkylation of enolate anion

11 Nucleophilic reactions involving enolate anions Alkylation of enolate anion

12 Nucleophilic reactions involving enolate anions Addition-dehydration: Aldol reaction Carbonyl compounds reacting as electrophiles -> aldol reaction Aldehydes are better electrophiles than ketons -> aldol reaction more favourable with aldehydes

13 Nucleophilic reactions involving enolate anions Addition-dehydration: Aldol reaction mixed aldol reaction

14 Nucleophilic reactions involving enolate anions Addition-dehydration: Aldol reaction Product from aldol reaction dehydrates by heating in acid or base -> α,β unsaturated carbonyl compound Under basic conditions -> E1cb (elimination-unimolecular-conjugated base)

15 Nucleophilic reactions involving enolate anions Addition-dehydration: Aldol reaction Intramolecular aldol reaction

16 Nucleophilic reactions involving enolate anions Other stabilized anions as nucleophiles: nitriles and nitromethane

17 Nucleophilic reactions involving enolate anions Other stabilized anions as nucleophiles: nitriles and nitromethane

18 Nucleophilic reactions involving enolate anions Other stabilized anions as nucleophiles: nitriles and nitromethane

19 Nucleophilic reactions involving enolate anions Enamines as nucleophiles

20 Nucleophilic reactions involving enolate anions Enamines as nucleophiles

21 Nucleophilic reactions involving enolate anions Enamines as nucleophiles

22 Nucleophilic reactions involving enolate anions Enolate anions from carboxylic acid derivates

23 Nucleophilic reactions involving enolate anions Enolate anions from carboxylic acid derivates base More favourable with ketons and aldehydes

24 Nucleophilic reactions involving enolate anions Enolate anions from carboxylic acid derivates

Feedback: Privacy Policy Feedback
Do Not Sell My Personal Information
About project: SlidePlayer Terms of Service

© 2025 SlidePlayer.com. Inc. All rights reserved.