Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids3h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

16. Conjugated Systems

Cope Rearrangement

Organic Chemistry

16. Conjugated Systems

Cope Rearrangement

Problem 22aMullins - 1st Edition

Textbook Question

(•) Predict the product of the Cope reactions shown. (a)

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Identify the structure of the starting material, which is typically an N-oxide of a tertiary amine.

Recognize that the Cope elimination involves a syn-elimination mechanism, where the N-oxide acts as an intramolecular oxidant.

Locate the β-hydrogens relative to the N-oxide group in the starting material, as these are the hydrogens that will be eliminated.

Draw the transition state, which involves a six-membered cyclic transition state where the β-hydrogen is transferred to the oxygen of the N-oxide, forming a double bond.

Predict the product by forming an alkene between the α and β carbons, and removing the N-oxide group, resulting in the formation of an alkene and a hydroxylamine.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Cope Rearrangement

The Cope rearrangement is a thermal reaction involving the rearrangement of 1,5-hexadienes to form new isomeric products. This reaction is a sigmatropic rearrangement, where the movement of sigma bonds occurs in a concerted manner, typically resulting in a shift of the double bond positions. Understanding the mechanism and stereochemistry of this rearrangement is crucial for predicting the products accurately.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of Cope reactions, the stereochemical configuration of the starting materials can influence the outcome of the reaction, leading to different stereoisomers. Recognizing the stereochemical implications is essential for predicting the correct product structure.

Thermal vs. Photochemical Reactions

Cope rearrangements are typically thermal reactions, meaning they occur at elevated temperatures without the need for light. This contrasts with photochemical reactions, which are driven by light energy. Understanding the conditions under which the Cope rearrangement occurs helps in predicting the reaction pathway and the stability of the products formed.

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