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

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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2:39 minutes

Problem 17b

Textbook Question

What is the product of each of the following reactions?
b.

Verified step by step guidance

Step 1: Recognize the reaction type. This is a typical example of a cross-coupling reaction, specifically a Heck reaction. The Heck reaction involves the coupling of an aryl or vinyl halide (in this case, an aryl iodide) with an alkene in the presence of a palladium catalyst and a base.

Step 2: Identify the reactants. The aryl iodide is a substituted cyclopentene ring with an iodine atom attached. The alkene is a terminal alkene with a methyl group attached to the double bond.

Step 3: Understand the mechanism. In the Heck reaction, the palladium catalyst facilitates the oxidative addition of the aryl halide to form a palladium-aryl complex. The alkene then coordinates to the palladium center, followed by migratory insertion of the alkene into the palladium-aryl bond.

Step 4: Predict the regioselectivity. The alkene will couple with the aryl group at the less sterically hindered position, forming a new C-C bond. The product will be a substituted alkene where the aryl group is attached to the terminal carbon of the alkene.

Step 5: Consider stereochemistry. The Heck reaction typically proceeds with retention of the double bond geometry in the alkene. The final product will retain the E-configuration of the alkene unless otherwise specified.

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Key Concepts

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

Organometallic Chemistry

Organometallic chemistry involves compounds containing metal-carbon bonds, where metals can be transition metals or main group elements. These compounds are crucial in various reactions, including cross-coupling reactions, where they facilitate the formation of carbon-carbon bonds. Understanding the role of organometallic reagents is essential for predicting the products of reactions involving these species.

Cross-Coupling Reactions

Cross-coupling reactions are a class of reactions in organic chemistry where two different organic groups are joined together using a metal catalyst. Common examples include the Suzuki and Heck reactions, which utilize palladium catalysts to couple aryl halides with alkenes or other nucleophiles. Recognizing the mechanism and conditions of these reactions is vital for determining the expected products.

Palladium Catalysis

Palladium catalysis is a key technique in organic synthesis, particularly in cross-coupling reactions. Palladium can exist in multiple oxidation states, allowing it to facilitate the transfer of groups between reactants. The choice of ligands and reaction conditions can significantly influence the efficiency and selectivity of the reaction, making it important to understand how these factors affect the outcome.

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Related Practice

Textbook Question

Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

(b)

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(e)

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(f)

Textbook Question

What products are obtained from metathesis of each of the following alkenes?

Textbook Question

What product is obtained from ring-opening metathesis polymerization of each of the following compounds? (Hint: In each case, the product is an unsaturated hydrocarbon with a high molecular weight.)

Textbook Question

What compound undergoes metathesis to form each of the following compounds?

Textbook Question

What products are obtained from metathesis of each of the following alkenes?

a. CH₃CH₂CH=CH₂

Textbook Question

What new products are obtained from metathesis of the following alkyne?

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