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

35. Transition Metals

Heck Reaction

Organic Chemistry

35. Transition Metals

Heck Reaction

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3:11 minutes

Problem 11eBruice - 8th Edition

Textbook Question

What vinylic halide couples with styrene (C6H5-CH=CH2) in order to synthesize each of the following compounds using a Heck reaction? c.

Verified step by step guidance

Identify the Heck reaction components: a vinylic halide and an alkene (styrene).

Recognize that the product is a substituted styrene with a cyclopentane group.

Determine the structure of the vinylic halide needed to couple with styrene to form the product.

Note that the vinylic halide should have a cyclopentane ring attached to the vinyl group.

Conclude that the vinylic halide is 1-bromo-1-cyclopentene, which couples with styrene to form the desired product.

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Key Concepts

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

Heck Reaction

The Heck reaction is a palladium-catalyzed coupling reaction between an aryl or vinyl halide and an alkene, resulting in the formation of substituted alkenes. This reaction is significant in organic synthesis for constructing complex molecules and is widely used in the pharmaceutical and materials industries. The reaction typically requires a base and a palladium catalyst to facilitate the coupling process.

Vinylic Halides

Vinylic halides are organic compounds where a halogen atom is bonded to a carbon atom that is part of a double bond (alkene). They are important intermediates in organic synthesis, particularly in reactions like the Heck reaction, where they can couple with alkenes to form more complex structures. Understanding the reactivity and properties of vinylic halides is crucial for predicting the outcomes of coupling reactions.

Alkene Reactivity

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond, making them more reactive than alkanes. Their reactivity is influenced by factors such as sterics and electronics, which affect how they participate in reactions like the Heck reaction. In this context, the ability of alkenes to undergo nucleophilic attack and form new carbon-carbon bonds is essential for synthesizing desired products.