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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3:52 minutes

Problem 29b

Textbook Question

What products would you expect from the following Suzuki coupling reactions?
(b)

Verified step by step guidance

Step 1: Recognize that this is a Suzuki coupling reaction, which involves the cross-coupling of an aryl or vinyl halide (in this case, bromobenzonorbornene) with an organoboron compound (in this case, pyridylboronic ester) in the presence of a palladium catalyst and a base.

Step 2: Identify the two key components: (1) the aryl halide (bromobenzonorbornene) and (2) the organoboron compound (pyridylboronic ester). The palladium catalyst (Pd(PPh₃)₄) facilitates the coupling, and NaOH serves as the base to activate the boronic ester.

Step 3: Understand the mechanism. The reaction proceeds via oxidative addition of the aryl halide to the palladium catalyst, followed by transmetalation with the organoboron compound, and finally reductive elimination to form the new C-C bond.

Step 4: Predict the product. The bromine atom on the bromobenzonorbornene is replaced by the pyridyl group from the boronic ester, resulting in a biaryl product where the pyridyl group is directly bonded to the benzonorbornene ring.

Step 5: Verify the regioselectivity and stereochemistry. Since the reaction involves sp² hybridized carbons, the product will be planar at the site of the new bond. The pyridyl group will attach to the position where the bromine was originally located.

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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 organoboron compound with a halogenated organic compound in the presence of a palladium catalyst and a base. This reaction is particularly valuable for synthesizing biaryl compounds and is favored for its mild reaction conditions and high functional group tolerance.

Organoboron Compounds

Organoboron compounds, such as boronic acids and boronate esters, are key reactants in Suzuki coupling reactions. They contain a boron atom bonded to a carbon atom, which can participate in nucleophilic attack during the coupling process. The stability and reactivity of these compounds make them essential for forming diverse organic molecules, especially in pharmaceutical and materials chemistry.

Palladium Catalysis

Palladium catalysis is crucial in facilitating the Suzuki coupling reaction. Palladium complexes, often in the form of Pd(0) or Pd(II), serve as catalysts that lower the activation energy required for the reaction to proceed. The palladium catalyst enables the oxidative addition of the halide to the palladium center, followed by transmetalation with the organoboron compound, ultimately leading to the formation of the desired product.

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