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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8:03 minutes

Problem 45a

Textbook Question

Metathesis of which of the following sets of alkenes leads to the highest yield of a single alkene?
1. 1-butene and 1-pentene
2. 2-butene and 3-hexene
3. 2-butene and 1-pentene

Verified step by step guidance

Step 1: Understand the concept of alkene metathesis. Alkene metathesis is a reaction where two alkenes exchange their alkylidene groups, forming new alkenes. The reaction is catalyzed by metal carbene complexes, and the product distribution depends on the stability and symmetry of the resulting alkenes.

Step 2: Analyze the given sets of alkenes. For each pair, consider the possible products of the metathesis reaction. The reaction involves breaking the double bonds of the alkenes and recombining the fragments to form new alkenes.

Step 3: Evaluate the stability of the potential products. The highest yield of a single alkene is achieved when the reaction favors the formation of a single, thermodynamically stable product. Symmetry and substitution patterns of the alkenes play a key role in determining the product distribution.

Step 4: For each pair of alkenes: (1) 1-butene and 1-pentene, (2) 2-butene and 3-hexene, and (3) 2-butene and 1-pentene, write the possible products of the metathesis reaction. Consider the substitution patterns of the resulting alkenes and their relative stabilities (e.g., more substituted alkenes are generally more stable).

Step 5: Compare the product distributions for each pair. Identify the pair that leads to the formation of a single, stable alkene as the major product. This pair will correspond to the highest yield of a single alkene.

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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, leading to the formation of new alkenes. This reaction is facilitated by catalysts, such as those based on molybdenum or tungsten, and is significant in organic synthesis for producing higher-value compounds. Understanding the mechanism and factors influencing the reaction is crucial for predicting the outcomes of different alkene combinations.

Thermodynamic Stability of Alkenes

The stability of alkenes is influenced by their degree of substitution; more substituted alkenes are generally more stable due to hyperconjugation and the inductive effect. In metathesis, the formation of more stable alkenes typically leads to higher yields. Recognizing the stability of the potential products formed from the metathesis reaction helps in determining which alkene pair will yield the most favorable outcome.

Selectivity in Metathesis Reactions

Selectivity in metathesis reactions refers to the preference for forming certain products over others based on the starting materials. Factors such as sterics, electronic effects, and the nature of the catalyst can influence selectivity. Analyzing the structure of the alkenes involved allows chemists to predict which combinations will yield a single, predominant alkene, thus maximizing the efficiency of the reaction.

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