Baeyer-Villiger Oxidation: Ketones to Esters Bronsted acid/base interaction: Carbonyl oxygen is protonated. This will generate a more reactive carbonyl.

Slides:

Advertisements

Similar presentations

Reactions of Ketones and Aldehydes Susan F. Hornbuckle Associate Professor of Chemistry Clayton State University.

Advertisements

Aldehyde and Ketone Reactions

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

Bromination of Benzene

Aldehydes and ketones that have a C=O bond , but no O-H bond, cannot form hydrogen bonds with one another, as alcohols. Aldehyde and ketones therefore.

Reactions of Alcohols Oxidation R-X, Ether, and Ester Preparation Protection of Alcohols Synthesis The Logic of Mechanisms.

© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 20 More About Oxidation–Reduction Reactions.

Chapter 11 Introduction to Organic Chemistry

Case Western Reserve University

Chapter 17 Reactions of Aromatic Compounds

Reactions of Aromatic Compounds

165 Chapter 20: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution 20.1: Nomenclature of Carboxylic Acid Derivatives (please read)

Organic Chemistry Reviews Chapter 16 Cindy Boulton April 5, 2009.

17.14 Stereoselective Addition to Carbonyl Groups Nucleophilic addition to carbonyl groups sometimes leads to a mixture of stereoisomeric products.

Nitrogen Based Carbonyl Reactions. Some reactions of aldehydes and ketones progress beyond the nucleophilic addition stage Acetal formation Imines Compounds.

Benzene Reactions Dr AKM Shafiqul Islam School of Bioprocess Engineering University Malaysia Perlis.

Molecules and Functional Groups

The Nature of the Active Site Questions we want to ask: 1.Looking at the reactants and products, what type of reaction has occurred Hydrolysis, Condensation,

Chapter 18 Carboxylic Acids and Their Derivatives

Introduction Structure of the Carbonyl Group

Alcohols and Ethers-2 Dr AKM Shafiqul Islam School of Bioprocess Engineering University Malaysia Perlis (UniMAP)

Physical Organic Chemistry CH-5 Addition & Rearrangement reactions Prepared By Dr. Khalid Ahmad Shadid Islamic University in Madinah Department of Chemistry.

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

Common Biochemical Reactions. chemical reaction  a process involving one, two or more substances (called reactants), characterized by a chemical change.

Nucleophilic addition – reaction of aldehydes and ketones C of C=O is delta positive (the most electrophilic centre). R groups are inductively donating.

Alcohols. Complete Combustion of Alcohols IB Chemistry SL CC23E83D555 Oxidation reactions.

Organic and biochemistry Assistancce Lecturer Amjad Ahmed Jumaa  Basicity of aromatic amines.  Concept the carbanions.  Methods of.

Hemiacetal and Acetal Functional Groups Hemiacetal: alcohol and ether on same carbon Acetal: Two ethers on same carbon.

Organics. Organic Structures Many materials that forensic scientists collect at a crime scene are organic in nature. Carbon atoms make the backbone of.

Reactions of Alkenes.

Carbocation Rearrangements

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic.

Chapter 4: Carbon and the Diversity of Life Organic molecules: molecules that contain carbon Carbon: valence of 4 form 4 covalent bonds Variations in carbon.

Revision Session Organic Chemistry.

NUCLEOPHILIC SUBSTITUTION REACTION CARBOXYLIC ACID AND ITS DERIVATIVES NUCLEOPHILIC ADDITION to a carbonyl group as the first step.

Guided by: H.S.Tailor Pacific school of engineering, Surat Sub :Application of following reaction with mechanism.

6.7 Nucleophiles and Electrophiles A major focus in this course is on predicting reaction products for ionic reactions and explaining HOW such reactions.

Aldehydes and ketones: nucleophilic addition reactions.

Chapter 16 Aldehydes and Ketones I

Chapter 16 Aldehydes and Ketones I

Aldehydes and Ketones Handout # 7 Winter 2015/2016 (N. Noureldin)

Chapter 14 Skeletal-Rearrangement Reactions Carbon-Carbon Rearrangements Carbon-Nitrogen Rearrangements Carbon-Oxygen Rearrangements Synthetic Applications.

Ch 16 Aldehydes and Ketones I. Introduction All aldehydes have a carbonyl group bonded on one side to a carbon and on the other to a hydrogen Examples:

Chap. 1 Solomons: Chapter 12 Alcohols from Carbonyl Compounds: Oxidation-Reduction and Organometallic Compounds.

Organic Chemistry Review

Reactions: OXIDATION & REDUCTION ROHAZITA BAHARI

Ch 17- Carboxylic Acids and their derivatives

The Molecules of Cells.

The Nature of the Active Site

FUNCTIONAL GROUPS IN BIOMOLECULES & BONDING CAPACITY

Figure Number: 17-00CO Title: Penicillin G

Move and label the protons, neutrons, and electrons to build an atom of each of the following elements.

Organic compounds contain carbon..excluding carbonates and oxides

Build An Atom Workshop: Hydrogen 1

Introduction Structure of the Carbonyl Group

Chapter 9 Aldehydes and Ketones: Nucleophilic Addition Reactions

Fundamentals of Organic Chemistry

Fundamentals of Organic Chemistry

Mechanism of Electrophilic Aromatic Substitution

Fundamentals of Organic Chemistry

Schedule Today (4/19): Chapter 21 Monday (4/22): Chapter 21

REACTIONS OF ALDEHYDES, KETONES AND CARBOXYLIC ACIDS

Fundamentals of Organic Chemistry

of carbonyl group chemistry

Organic Structure Among neutral (uncharged) organic compounds

Fundamentals of Organic Chemistry

Fundamentals of Organic Chemistry

Fundamentals of Organic Chemistry

Presentation transcript:

Baeyer-Villiger Oxidation: Ketones to Esters Bronsted acid/base interaction: Carbonyl oxygen is protonated. This will generate a more reactive carbonyl group

Baeyer-Villiger Oxidation: Ketones to Esters Nucleophilic Attack of the peroxy acid on the highly reactive carbonyl unit

Baeyer-Villiger Oxidation: Ketones to Esters Sigma bonding electron-pair migrates with the phenyl group to the electropositive oxygen centre. This in turn initiates reorganization of sigma- and pi- bonding electrons in the peroxy acid group. The PHENYL group migration is very reminiscent of the [1,2]-Methyl shift in carbocation rearrangements.

Baeyer-Villiger Oxidation: Ketones to Esters Positive charge on carbon is neutralized through the loss of the hydroxyl hydrogen as a PROTON

Baeyer-Villiger Oxidation: Ketones to Esters Phenyl acetate