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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2:36 minutes

Problem 30b

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)

Verified step by step guidance

Step 1: Identify the Suzuki reaction components. The Suzuki reaction involves coupling an aryl or vinyl halide (in this case, the brominated compound) with an organoboron compound in the presence of a palladium catalyst and a base.

Step 2: Determine the organoboron compound needed. To extend the chain and introduce the alkyl group, you need an alkylboronic acid or alkylboronate ester that matches the desired product's structure (e.g., a butylboronic acid or butylboronate).

Step 3: Set up the reaction conditions. Combine the brominated starting material, the organoboron compound, a palladium catalyst (e.g., Pd(PPh₃)₄), and a base (e.g., K₂CO₃ or NaOH) in a suitable solvent like tetrahydrofuran (THF) or water.

Step 4: Perform the Suzuki coupling reaction. Under the reaction conditions, the palladium catalyst facilitates the formation of a new carbon-carbon bond between the brominated compound and the alkyl group from the organoboron reagent.

Step 5: Purify the product. After the reaction is complete, isolate the desired product using techniques such as extraction, chromatography, or recrystallization to obtain the final compound with the extended alkyl 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 powerful method for forming carbon-carbon bonds, particularly between aryl or vinyl halides and organoboron compounds. This reaction typically requires a palladium catalyst and a base, allowing for the coupling of two organic fragments to create more complex molecules. It is widely used in organic synthesis for constructing biaryl compounds and other complex structures.

Organoboron Compounds

Organoboron compounds, such as boronic acids and boronate esters, are key reagents in the Suzuki reaction. They contain a boron atom bonded to a carbon atom, which can participate in nucleophilic attack during the coupling process. Their stability and reactivity make them ideal for forming new carbon-carbon bonds, facilitating the synthesis of diverse organic molecules.

Reaction Conditions

The success of the Suzuki reaction depends on specific reaction conditions, including the choice of solvent, temperature, and the presence of a base. Common solvents include water, ethanol, or toluene, while bases like sodium carbonate or potassium phosphate are often used to deprotonate the organoboron compound. Optimizing these conditions is crucial for achieving high yields and selectivity in the desired product.

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Related Practice

Textbook Question

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

(b)

Textbook Question

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

(a)

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)

Open Question

Determine the product from the following Suzuki Reaction.

Open Question

Predict the structures of organoborane compound A and coupling product B in the following reaction sequence.

Open Question

Beginning from 1-pentyne, synthesize the following compound via a Suzuki Coupling Reaction.

Multiple Choice

What is the name of the reaction which couples a carbon bound to a leaving group with a carbon bound to a B(OH)₂ group?

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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)

Key Concepts

Suzuki Coupling Reaction

Organoboron Compounds

Reaction Conditions

Watch next

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)