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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3:10 minutes

Problem 29a

Textbook Question

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

Verified step by step guidance

Step 1: Recognize that this is a Suzuki coupling reaction, which involves the cross-coupling of an aryl halide (in this case, a bromobenzene derivative) with an organoboron compound (in this case, a phenylboronic acid derivative) in the presence of a palladium catalyst and a base.

Step 2: Identify the two reactants. The aryl halide is 4-bromo-1-isopropylbenzene, and the organoboron compound is 4-methylphenylboronic acid. The palladium catalyst (Pd(OAc)₂) and base (K₃PO₄) facilitate the reaction.

Step 3: Understand the mechanism. The palladium catalyst first undergoes oxidative addition with the aryl halide, forming a palladium complex. The organoboron compound then reacts with the palladium complex via transmetalation, transferring the aryl group from boron to palladium.

Step 4: The final step is reductive elimination, where the two aryl groups (one from the aryl halide and one from the organoboron compound) couple together, forming a new carbon-carbon bond. This results in the formation of a biaryl product.

Step 5: Combine the two aryl groups. The product of this reaction will be 4-isopropyl-1-(4-methylphenyl)benzene, where the isopropyl group and methyl group remain intact on their respective benzene rings.

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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, which are important in pharmaceuticals and materials science.

Palladium Catalysis

Palladium catalysis is crucial in many cross-coupling reactions, including the Suzuki reaction. Palladium serves as a catalyst that facilitates the oxidative addition of the halide to the palladium center, followed by transmetalation with the organoboron compound. The use of palladium allows for milder reaction conditions and higher selectivity in forming desired products.

Transmetalation

Transmetalation is a key step in the Suzuki coupling mechanism where the organoboron compound transfers its organic group to the palladium complex. This step is essential for forming the new carbon-carbon bond. The efficiency of transmetalation can be influenced by the choice of base and the nature of the organoboron compound, impacting the overall yield of the reaction.

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Related Practice

Textbook Question

What are the products of the following reactions?

Textbook Question

Using ethynylcyclohexane as a starting material and any other needed reagents, how can the following compounds be synthesized?

Textbook Question

What is the product of each of the following reactions?

Textbook Question

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

(b)

Textbook Question

Show how you would use a Suzuki reaction to synthesize the following biaryl compound. As starting materials, you may use the two indicated compounds, plus any additional reagents you need.

Textbook Question

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

(a)

Textbook Question

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

(b)

Open Question

Determine the product from the following Suzuki Reaction.

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