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

19. Reactions of Aromatics: EAS and Beyond

Benzene Reactions

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Benzene Reactions

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4:00 minutes

Problem 55d,e

Textbook Question

What products would you expect from the following coupling reactions?
(d)
(e)

Verified step by step guidance

Step 1: Identify the type of coupling reaction. The first reaction involves a bromobenzene derivative and a boronic ester, which suggests a Suzuki coupling reaction. The second reaction involves a bromonaphthalene derivative and a nitro-substituted styrene, which suggests a Heck coupling reaction.

Step 2: For the Suzuki coupling reaction, the palladium catalyst facilitates the cross-coupling between the aryl bromide and the boronic ester. The base activates the boronic ester, allowing it to react with the aryl bromide. The product will be a new C-C bond formed between the phenyl group and the alkene chain attached to the boron.

Step 3: For the Heck coupling reaction, the palladium catalyst and base facilitate the formation of a C-C bond between the aryl bromide and the alkene. The nitro-substituted styrene will couple with the bromonaphthalene derivative, forming a new C-C bond at the β-position of the alkene relative to the nitro group.

Step 4: Consider regioselectivity and stereochemistry. In the Suzuki reaction, the product will retain the stereochemistry of the alkene in the boronic ester. In the Heck reaction, the product will likely favor the trans configuration of the alkene due to steric and electronic factors.

Step 5: Write the final structures of the products. For the Suzuki reaction, the product will be a phenyl group attached to the alkene chain. For the Heck reaction, the product will be a naphthalene group attached to the β-position of the nitro-substituted styrene alkene.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Coupling Reactions

Coupling reactions are organic reactions where two fragments are joined together, typically involving the formation of a new carbon-carbon bond. These reactions are crucial in organic synthesis, particularly in the formation of complex molecules. Common types include Suzuki, Heck, and Sonogashira reactions, each utilizing different reagents and conditions to achieve the desired product.

Reactivity of Functional Groups

Understanding the reactivity of functional groups is essential in predicting the outcomes of coupling reactions. Different functional groups, such as halides, alcohols, and amines, have distinct reactivity patterns that influence how they participate in reactions. Recognizing these patterns helps in determining which groups can effectively couple and what products will form.

Mechanism of Reactions

The mechanism of a reaction outlines the step-by-step process by which reactants are converted into products. In coupling reactions, mechanisms often involve the formation of intermediates and the breaking and forming of bonds. A clear understanding of these mechanisms allows chemists to predict reaction outcomes and optimize conditions for desired products.

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