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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4:06 minutes

Problem 26

Textbook Question

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

Verified step by step guidance

Step 1: Identify the alkyne structure provided in the image. The molecule contains a triple bond between two carbon atoms, with substituents on either side. The substituents are an ethyl group on one side and an isopropyl group on the other side.

Step 2: Understand the concept of alkyne metathesis. Alkyne metathesis is a reaction where triple bonds are redistributed between alkyne molecules, typically catalyzed by metal-based catalysts such as molybdenum or tungsten complexes.

Step 3: Predict the products of the metathesis reaction. During metathesis, the triple bond is cleaved and reformed, leading to the exchange of substituents between the reacting alkyne molecules. This results in the formation of new alkynes with different substituent arrangements.

Step 4: Analyze the possible combinations of substituents. In this case, the ethyl and isopropyl groups can recombine with other fragments of the molecule, leading to the formation of two new alkynes. The products will depend on the redistribution of the substituents.

Step 5: Write the general structures of the new products. The new alkynes formed will have the triple bond between carbon atoms, with one product containing an ethyl group and another substituent, and the second product containing an isopropyl group and another substituent. The exact structures can be determined by considering the redistribution of substituents during the reaction.

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Key Concepts

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

Alkyne Structure

Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond. This structure is characterized by the presence of sp-hybridized carbon atoms, which leads to linear geometry around the triple bond. Understanding the specific alkyne structure is crucial for predicting the products of reactions such as metathesis.

Metathesis Reaction

Metathesis is a chemical reaction that involves the exchange of partners between two reactants, typically involving alkenes or alkynes. In the context of alkynes, metathesis can lead to the formation of new carbon-carbon bonds, resulting in different alkyne or alkene products. This reaction is facilitated by catalysts, often involving transition metals.

Catalysts in Organic Reactions

Catalysts are substances that increase the rate of a chemical reaction without being consumed in the process. In organic chemistry, catalysts such as transition metal complexes are often used in metathesis reactions to facilitate the breaking and forming of bonds. Understanding the role of catalysts is essential for predicting the efficiency and outcome of metathesis reactions.

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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

Textbook Question

Draw the product of ring-closing metathesis for each of the following compounds:

Textbook Question

What starting material is required in order to synthesize each of the following compounds by ring-closing metathesis?

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Textbook Question

Using the epoxide shown, addition of an organolithium reagent, when followed by an acid quench, produces only the starting epoxy alcohol. Why? How could the reaction be modified to produce the desired molecule? [Hint: Look back at Section 13.14.]

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