22.7 Cope Elimination
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- 4.1a Nomenclature of Alkanes
- 4.1b Nomenclature of Cycloalkanes
- 4.1c Systematic Nomenclature of Complex Substituents
- 4.1d Common Names of Complex Substituents
- 4.1e Nomenclature of Bicyclic Compounds
- 4.2 Drawing Constitutional Isomers
- 4.3 Newman Projections
- 4.4 Cycloalkanes and Cyclohexane Chair Conformations
- 5.1 Overview of Isomerism
- 5.2 Chiral Centers and Chirality
- 5.3 Absolute Configurations Assigning R and S
- 5.4 Molecules with Multiple Chiral Centers
- 5.5 Fischer Projections
- 5.6 Determining the Relationship Between a Pair of Molecules
- 5.7 Amine Inversion and Chiral Molecules Without Chiral Centers
- 5.8 Optical Activity
- 7.1a Introduction to SN2 Reactions
- 7.1b Factors Affecting SN2 Reactions
- 7.2a Introduction to SN1 Reactions
- 7.2b Carbocation Rearrangements in SN1 Reactions
- 7.2c Racemization in SN1 Reactions
- 7.2d Factors Affecting SN1 Reactions
- 7.3 Unreactivity of Vinyl and Aryl Halides
- 7.4 Predicting the Products of Substitution Reactions
- 7.5 Nomenclature of Alkenes
- 7.6 Stability of Alkenes
- 7.7a Introduction to E2 Elimination Reactions
- 7.7b Exceptions to Zaitsev’s Rule for E2 Reactions
- 7.7c The Stereospecificity of E2 Reactions Anti periplanar
- 7.8 Introduction to E1 Elimination Reactions
- 7.9 Predicting the Products of Elimination Reactions
- 7.10 Distinguishing Between Substitution and Elimination Reactions
- 8.1 Introduction to Alkene Addition Reactions
- 8.2 Hydrohalogenation
- 8.3a Hydration Acid Catalyzed Hydration
- 8.3b Hydration Oxymercuration Demercuration
- 8.3c Hydration Hydroboration Oxidation
- 8.4a Acid Catalyzed Addition of an Alcohol
- 8.4b Alkoxymercuration Demercuration
- 8.5 Catalytic Hydrogenation
- 8.6a Halogenation
- 8.6b Halohydrin Formation
- 8.7a Anti Dihydroxylation
- 8.7b Syn Dihydroxylation
- 8.8 Predicting the Products of Alkene Addition Reactions
- 8.9 Oxidative Cleavage Ozonolysis and Permanganate Cleavage
- 9.1 Nomenclature of Alkynes
- 9.2 Acidity of Alkynes
- 9.3 Preparation of Alkynes
- 9.4 Reduction of Alkynes
- 9.5 Introduction to Addition Reactions of Alkynes
- 9.6 Hydrohalogenation
- 9.7 Halogenation
- 9.8a Acid Catalyzed Hydration
- 9.8b Hydroboration Oxidation
- 9.8c Keto Enol Tautomerization
- 9.9 Ozonolysis
- 9.10 Alkylation of Acetylide Ions
- 11.1 Functional Group Conversions
- 11.2 Increasing the Length of the Carbon Skeleton
- 11.3 Decreasing the Length of the Carbon Chain or Opening a Ring
- 11.4a Common Patterns in Synthesis Part 1
- 11.4b Common Patterns in Synthesis Part 2
- 11.4c Common Patterns in Synthesis Part 3
- 11.4d Common Patterns in Synthesis Part 4
- 12.1 Properties and Nomenclature of Alcohols
- 12.2 Acidity of Alcohols and Phenols
- 12.3a Synthesis of Alcohols; Reduction of Ketones and Aldehydes
- 12.3b Synthesis of Alcohols; Grignard Addition
- 12.4 Protecting Alcohols
- 12.5a Reaction with HCl, HBr, and HI
- 12.5b Substitution with PBr3 and SOCl2
- 12.5c Formation of Tosylate Esters
- 12.6 Elimination Dehydration
- 12.7 Oxidation with Chromic Acid and PCC
- 14.1 Introduction to IR Spectroscopy
- 14.2a IR Spectra of Carbonyl Compounds
- 14.2b The Effect of Conjugation on the Carbonyl Stretching Frequency
- 14.3 Interpreting More IR Spectra
- 14.4 Introduction to Mass Spectrometry
- 14.5 Isotope Effects in Mass Spectrometry
- 14.6a Fragmentation Patterns of Alkanes, Alkenes, and Aromatic Compounds
- 14.6b Fragmentation Patterns of Alkyl Halides, Alcohols, and Amines
- 14.6c Fragmentation Patterns of Ketones and Aldehydes
- 15.1 Introduction to NMR
- 15.2 The Number of Signals in C 13 NMR
- 15.3 The Number of Signals in Proton NMR
- 15.4 Homotopic vs Enantiotopic vs Diastereotopic
- 15.5a The Chemical Shift in C 13 and Proton NMR
- 15.5b The Integration or Area Under a Signal in Proton NMR
- 15.5c The Splitting or Multiplicity in Proton NMR
- 15.6a Interpreting NMR Example 1
- 15.6b Interpreting NMR Example 2
- 15.6c Interpreting NMR Example 3
- 15.6d Structural Determination From All Spectra Example 4
- 15.6e Structural Determination From All Spectra Example 5
- 15.7 Complex Splitting
- 16.1 Introduction to Conjugated Systems and Heats of Hydrogenation
- 16.2a Introduction to Pi Molecular Orbitals Ethylene
- 16.2b Pi Molecular Orbitals 1,3 Butadiene
- 16.2c Pi Molecular Orbitals the Allyl System
- 16.2d Pi Molecular Orbitals 1,3,5 Hexatriene
- 16.3 UV Vis Spectroscopy
- 16.4 Addition Reactions to Conjugated Dienes
- 16.5a Introduction to Diels Alder Reactions
- 16.5b Stereoselectivity and Regioselectivity in Diels Alder Reactions
- 16.5c Diels Alder Reactions with Cyclic Dienes
- 16.5d Conservation of Orbital Symmetry in Diels Alder Reactions
- 16.6 Cycloaddition Reactions
- 16.7 Electrocyclic Reactions
- 16.8 Sigmatropic Rearrangements
- 18.1 Introduction to Aromatic Substitution Reactions
- 18.2a EAS Bromination and Chlorination
- 18.2b EAS Sulfonation and Desulfonation
- 18.2c EAS Nitration
- 18.2d EAS Friedel Crafts Alkylation and Acylation
- 18.2e EAS Activating and Deactivating Groups and Ortho Para and Meta Directors
- 18.2f EAS Predicting the Products of EAS Reactions
- 18.3 Catalytic Hydrogenation and the Birch Reduction
- 18.4a Side Chain Oxidation with Permanganate or Chromic Acid
- 18.4b Benzylic Bromination with NBS
- 18.4c The Clemmensen and Wolff Kishner Reductions
- 18.4d Side Chain General Reduction
- 18.5 Nucleophilic Aromatic Substitution
- 19.1 Nomenclature of Ketones and Aldehydes
- 19.2 Synthesis of Ketones and Aldehydes
- 19.3 Introduction to Nucleophilic Addition Reactions
- 19.4 Hydration Addition of Water
- 19.5a Addition of Alcohols
- 19.5b Cyclic Acetals as Protecting Groups
- 19.6a Addition of Primary Amines Imine Formation
- 19.6b Addition of Secondary Amines Enamine Formation
- 19.6c Mechanism for the Wolff Kishner Reduction
- 19.7 Reduction via Thioacetals
- 19.8 Hydride Reduction Reactions
- 19.9a Addition of Acetylide Ions and Grignard Reagents
- 19.9b Addition of HCN Cyanohydrin Formation
- 19.9c The Wittig Reaction
- 19.10 Baeyer Villiger Oxidation
- 20.1 Introduction to and Physical Properties of Carboyxylic Acids and Acid Derivatives
- 20.2a Nomenclature of Carboxylic Acids
- 20.2b Nomenclature of Acid Halides
- 20.2c Nomenclature of Acid Anhydrides
- 20.2d Nomenclature of Esters
- 20.2e Nomenclature of Amides
- 20.2f Nomenclature of Nitriles
- 20.3 Introduction to Nucleophilic Acyl Substitution
- 20.4 Reaction with Organometallic Reagents
- 20.5 Hydride Reduction
- 20.6 Interconversion of Carboxylic Acids and Derivatives
- 20.7 The Mechanisms of Nucleophilic Acyl Substitution
- 20.8a Synthesis of Acid Halides
- 20.8b Reactions of Acid Halides
- 20.9 Synthesis and Reactions of Acid Anhydrides
- 20.10a Synthesis of Esters
- 20.10b Reactions of Esters
- 20.11 Synthesis and Reactions of Carboxylic Acids
- 20.12 Synthesis and Reactions of Amides
- 20.13 Synthesis and Reactions of Nitriles
- 21.1 Acidity of the Alpha Hydrogen
- 21.2 General Mechanisms of Alpha Substitution Reactions
- 21.3a Alpha Halogenation
- 21.3b The Haloform Reaction
- 21.3b The HVZ Reaction
- 21.4a Alpha Alkylation
- 21.4b The Stork Synthesis
- 21.5a Introduction to Aldol Reactions
- 21.5b Mechanisms of Aldol Reactions
- 21.5c Mixed Aldol Reactions
- 21.5d Intramolecular Aldol Reactions
- 21.6a Claisen Condensation Reactions
- 21.6b Dieckmann Condensation Reactions
- 21.7a Beta Decarboxylation
- 21.7b The Malonic Ester Synthesis
- 21.8 Michael Reactions
- 21.9 The Robinson Annulation
- 22.1 Classification of Amines
- 22.2 Nomenclature of Amines
- 22.3 Basicity of Amines
- 22.4a Synthesis of Amines Reduction
- 22.4b Synthesis of Amines Hofmann Rearrangement
- 22.4c Synthesis of Amines Curtius Rearrangement and Schmidt Reaction
- 22.4d Synthesis of Amines Gabriel Synthesis
- 22.4e Synthesis of Amines Reductive Amination
- 22.5 Acylation
- 22.6 Hofmann Elimination
- 22.7 Cope Elimination
- 22.8a Reaction with Nitrous Acid and the Sandmeyer Reactions
- 22.8b Azo Coupling
- 22.9 EAS Reactions with Nitrogen Heterocycles
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Cope Elimination
The Cope Elimination is an elimination reaction specifically for tertiary amines for which the major organic product is an alkene. The leaving group involved (a hydroxyl amine) is a moderate base and therefore is not a good leaving group. As a result, the major product is the Hofmann product (a.k.a. anti-Zaitsev product--the least substituted alkene). An explanation for why a poor leaving group results in the Hofmann product can be found here: 7.7b Exceptions to Zaitsev’s Rule for E2 Reactions.
Cope Elimination Mechanism
The Cope Elimination occurs over the course of two steps:
- Step 1 - Oxidation -- The oxidation of a tertiary amine to an amine oxide using hydrogen peroxide.
- Step 2 Elimination - The amine oxide produced in step 1 undergoes E2 elimination. This step is unique in that the oxide portion of the leaving group serves as the base involved in the elimination reaction.
