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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4:03 minutes

Problem 37d

Textbook Question

What are the products of the following reactions?
d.

Verified step by step guidance

Step 1: Analyze the starting material and reagents. The starting material is an aryl iodide (1-iodo-4-ethylbenzene). The reaction involves three steps: (1) treatment with lithium (Li), (2) reaction with a borate ester (B(OR)3), and (3) a Suzuki coupling reaction with a vinyl bromide in the presence of Pd(PPh3)4 and Na2CO3 under heat.

Step 2: In the first step, lithium reacts with the aryl iodide to form an aryl lithium intermediate. This is a nucleophilic species where the iodine atom is replaced by lithium.

Step 3: In the second step, the aryl lithium intermediate reacts with the borate ester (B(OR)3) to form an aryl boronic ester. This is a key intermediate for Suzuki coupling reactions.

Step 4: In the third step, the aryl boronic ester undergoes a Suzuki coupling reaction with the vinyl bromide. The palladium catalyst (Pd(PPh3)4) facilitates the cross-coupling between the aryl group and the vinyl group, forming a new C-C bond.

Step 5: The final product is a styrene derivative where the aryl group (4-ethylphenyl) is connected to the vinyl group (CH=CH2). This product is formed through the combination of the aryl boronic ester and the vinyl bromide.

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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 a boronic acid or boronate ester with an organic halide in the presence of a palladium catalyst and a base. This reaction is particularly valuable for synthesizing biaryl compounds and is characterized by its mild reaction conditions and high functional group tolerance.

Organoboron Compounds

Organoboron compounds, such as boronic acids and boronate esters, are key intermediates in various organic reactions, including the Suzuki reaction. They contain a boron atom bonded to a carbon atom, which can participate in nucleophilic substitution reactions. Their ability to form stable complexes with transition metals makes them essential for cross-coupling reactions, facilitating the formation of new carbon-carbon bonds.

Palladium Catalysis

Palladium catalysis plays a crucial role in many cross-coupling reactions, including the Suzuki reaction. Palladium serves as a catalyst that facilitates the oxidative addition of the organic halide and the subsequent reductive elimination to form the desired product. The use of palladium allows for lower activation energy and increased reaction rates, making it a preferred choice in synthetic organic chemistry.

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