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

Suzuki Reaction

Organic Chemistry

35. Transition Metals

Suzuki Reaction

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4:02 minutes

Problem 14c

Textbook Question

What aryl or vinylic halides would you use to synthesize the following compounds, using the alkenylorganoboron compound shown here?

c.

Verified step by step guidance

Step 1: Analyze the alkenylorganoboron compound provided in the image. The compound contains a boronic ester group attached to an alkenyl group, which can participate in Suzuki coupling reactions. Suzuki coupling is a palladium-catalyzed cross-coupling reaction between an organoboron compound and an aryl or vinylic halide.

Step 2: Examine the target compound shown in the image. The target molecule contains a conjugated system with an aryl group and an extended alkenyl chain. This suggests that the reaction involves coupling the alkenylorganoboron compound with an appropriate halide to form the desired structure.

Step 3: Identify the halide required for the coupling reaction. The target molecule has a phenyl group attached to the alkenyl chain. To achieve this, an aryl halide, such as bromobenzene or iodobenzene, can be used as the coupling partner.

Step 4: Consider the reaction conditions. The Suzuki coupling typically requires a palladium catalyst (e.g., Pd(PPh3)4), a base (e.g., K2CO3 or NaOH), and a solvent such as tetrahydrofuran (THF) or water. These conditions facilitate the formation of the C-C bond between the alkenylorganoboron compound and the aryl halide.

Step 5: Summarize the synthesis. To synthesize the target compound, use the alkenylorganoboron compound provided in the image and an aryl halide, such as bromobenzene or iodobenzene, under Suzuki coupling conditions. This will result in the formation of the desired conjugated system with the phenyl group attached to the alkenyl chain.

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Key Concepts

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

Suzuki Coupling Reaction

The Suzuki coupling reaction is a widely used method in organic chemistry for forming carbon-carbon bonds. It involves the reaction of an aryl or vinylic halide with an alkenylorganoboron compound in the presence of a palladium catalyst and a base. This reaction is particularly valuable for synthesizing complex organic molecules, allowing for the introduction of various functional groups.

Aryl and Vinylic Halides

Aryl halides are compounds where a halogen atom is bonded to an aromatic ring, while vinylic halides have a halogen atom attached to a carbon-carbon double bond. Both types of halides are important in organic synthesis, especially in reactions like the Suzuki coupling, where they serve as electrophiles that react with nucleophilic organoboron compounds to form new carbon-carbon bonds.

Alkenylorganoboron Compounds

Alkenylorganoboron compounds are organoboron species that contain a carbon-carbon double bond. They act as nucleophiles in the Suzuki reaction, reacting with aryl or vinylic halides to form new alkenes. The versatility of these compounds allows for the synthesis of a wide range of products, making them essential in the development of pharmaceuticals and advanced materials.

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