22.7 Cope Elimination
Chad's Organic Chemistry Videos
Course Menu
- 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
Chad's Ultimate Organic Chemistry Prep
Mastery Through Practice
- 60 Quizzes Arranged by Topic
- 15 Chapter Tests
- 3 Practice Final Exams
- Over 800 Questions
- Detailed Solutions
- Summary of Organic Reactions
- Ochem Study Guides
FREE Trial -- Chad's Ultimate Organic Chemistry Prep
Free Trial includes:
Complete Summary of Organic Reactions (downloadable)
All videos, study guides, and quizzes for chapters 1 and 2
Try before you buy!
Subscribe
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.
