Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
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 Acids4h 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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3:02 minutes

Problem 42b

Textbook Question

For those compounds that can be prepared by a Heck reaction, what starting materials are required?

Verified step by step guidance

Step 1: Understand the Heck reaction. The Heck reaction is a palladium-catalyzed coupling reaction between an aryl or vinyl halide and an alkene, forming a substituted alkene. It requires a palladium catalyst, a base, and typically proceeds via a syn addition mechanism.

Step 2: Analyze the target compound provided in the image. The compound consists of a biphenyl structure where one phenyl ring is directly attached to a cyclohexene ring. This suggests that the Heck reaction could be used to form the bond between the phenyl group and the cyclohexene ring.

Step 3: Identify the starting materials. For the Heck reaction, you need an aryl halide (such as bromobenzene or iodobenzene) and an alkene. In this case, the alkene would be cyclohexene, which has the double bond necessary for the reaction.

Step 4: Consider the reaction conditions. The reaction would require a palladium catalyst (e.g., Pd(PPh3)4), a base (e.g., triethylamine or potassium carbonate), and a solvent (e.g., DMF or acetonitrile). The reaction typically occurs under mild heating.

Step 5: Plan the reaction. Combine the aryl halide (e.g., bromobenzene) and cyclohexene in the presence of the palladium catalyst, base, and solvent. The Heck reaction will form the desired product by coupling the phenyl group to the cyclohexene ring.

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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 that forms carbon-carbon bonds between aryl halides and alkenes. This reaction is significant in organic synthesis for constructing complex molecules, particularly in the pharmaceutical and materials industries. Understanding the mechanism involves recognizing the role of the palladium catalyst and the formation of an aryl-palladium intermediate.

Starting Materials

In the context of the Heck reaction, the starting materials typically include an aryl halide (such as bromobenzene) and an alkene (like styrene). The choice of these materials is crucial as they determine the structure of the final product. The reactivity of the aryl halide and the nature of the alkene influence the efficiency and selectivity of the reaction.

Catalysis

Catalysis is a process that increases the rate of a chemical reaction by using a substance called a catalyst, which is not consumed in the reaction. In the Heck reaction, palladium serves as the catalyst, facilitating the formation of the carbon-carbon bond. Understanding catalysis is essential for grasping how the Heck reaction operates and how to optimize conditions for desired outcomes.

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