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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3:11 minutes

Problem 30a

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)

Verified step by step guidance

Step 1: Identify the Suzuki reaction components. The Suzuki reaction involves coupling an organoboron compound with an organohalide (such as bromides) in the presence of a palladium catalyst and a base. In this case, the starting material is an alkyl bromide, and the product contains a substituted benzene ring.

Step 2: Prepare the organoboron compound. To synthesize the desired product, you need an organoboron reagent that matches the substituent on the benzene ring. In this case, you would use an alkylboronic acid or alkylboronate ester with the same alkyl chain as the product (e.g., butylboronic acid).

Step 3: Set up the Suzuki coupling reaction. Combine the alkyl bromide starting material with the organoboron compound in the presence of a palladium catalyst (e.g., Pd(PPh3)4) and a base (e.g., K2CO3 or NaOH) in a suitable solvent such as tetrahydrofuran (THF) or water.

Step 4: Ensure the reaction conditions are optimized. Heat the reaction mixture gently to promote the coupling reaction, typically at 50–80°C. The palladium catalyst facilitates the formation of the carbon-carbon bond between the alkyl group and the benzene ring.

Step 5: Purify the product. After the reaction is complete, isolate the product by standard organic workup techniques, such as extraction, drying, and purification via column chromatography or recrystallization, to obtain the desired substituted benzene compound.

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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 an organic halide in the presence of a palladium catalyst and a base. This reaction is particularly valuable for synthesizing biaryl compounds, as it allows for the coupling of aryl groups, which is essential in the production of complex organic molecules.

Organoboron Compounds

Organoboron compounds are organic molecules that contain boron atoms bonded to carbon. They are key intermediates in the Suzuki reaction, typically used as nucleophiles. Common examples include arylboronic acids and esters, which can react with various electrophiles, such as aryl halides, to form new carbon-carbon bonds, facilitating the synthesis of complex structures.

Palladium Catalysis

Palladium catalysis is crucial in many cross-coupling reactions, including the Suzuki reaction. Palladium serves as a catalyst that facilitates the transfer of the aryl group from the organoboron compound to the organic halide. The catalytic cycle involves several steps, including oxidative addition, transmetalation, and reductive elimination, which ultimately lead to the formation of the desired product while regenerating the palladium catalyst.

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