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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5:02 minutes

Problem 22b

Textbook Question

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

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Identify the structure of the given alkene. Metathesis reactions involve the exchange of alkylidene groups between alkenes, so understanding the starting material is crucial.

Write the general reaction for alkene metathesis. In this reaction, two alkenes exchange their alkylidene groups to form new alkenes. Represent the starting alkene as R1-CH=CH-R2.

Break the double bond in the alkene and consider the possible recombination of the fragments. For example, R1-CH= and =CH-R2 can recombine to form new alkenes.

Determine the possible products by pairing the fragments in all possible combinations. For example, R1-CH=CH-R1 and R2-CH=CH-R2 could be potential products.

Verify the stability of the products and ensure that the reaction follows the principles of metathesis. Consider factors such as steric hindrance and the formation of stable alkenes.

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Key Concepts

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

Alkene Metathesis

Alkene metathesis is a chemical reaction that involves the exchange of alkyl groups between alkenes, resulting in the formation of new alkenes. This reaction is typically catalyzed by transition metal complexes, such as those containing molybdenum or tungsten. The process is valuable in organic synthesis for creating complex molecules and can lead to a variety of products depending on the starting alkenes.

Catalysts in Metathesis

Catalysts play a crucial role in alkene metathesis by lowering the activation energy required for the reaction to occur. Common catalysts include Grubbs and Schrock catalysts, which facilitate the breaking and forming of carbon-carbon double bonds. The choice of catalyst can influence the selectivity and efficiency of the reaction, affecting the types of products formed.

Product Distribution

The distribution of products in alkene metathesis depends on the structure of the starting alkenes and the reaction conditions. Factors such as sterics, electronic effects, and the presence of substituents can influence which alkenes are formed. Understanding the mechanism of metathesis helps predict the major and minor products, which is essential for effective synthetic planning.

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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.

(d)

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 is the product of each of the following reactions?

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

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