1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
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 Acids3h 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

35. Transition Metals

Heck Reaction

Organic Chemistry

35. Transition Metals

Heck Reaction

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2:29 minutes

Problem 11fBruice - 8th Edition

Textbook Question

a. Which of the following compounds cannot be prepared by a Heck reaction?

Verified step by step guidance

Identify the Heck reaction: It is a palladium-catalyzed coupling reaction between an alkene and an aryl or vinyl halide.

Examine compound A: It is a simple diene, which can be formed by coupling two alkenes, a possible outcome of a Heck reaction.

Examine compound B: It is a 1,4-diene, which can also be formed by coupling two alkenes, a possible outcome of a Heck reaction.

Examine compound C: It contains a carbonyl group adjacent to the double bond, which is not typically formed in a Heck reaction as it involves coupling with aryl or vinyl halides.

Conclude that compound C cannot be prepared by a Heck reaction due to the presence of the carbonyl group, which is not a typical product of this reaction.

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Key Concepts

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

Heck Reaction

The Heck reaction is a palladium-catalyzed coupling reaction between an aryl or vinyl halide and an alkene, resulting in the formation of substituted alkenes. This reaction is significant in organic synthesis for constructing complex molecules and is particularly useful for forming carbon-carbon bonds. Understanding the mechanism and the types of substrates that can participate is crucial for predicting the products formed.

Substrate Compatibility

In the context of the Heck reaction, substrate compatibility refers to the structural features of the reactants that allow for successful coupling. Factors such as steric hindrance, electronic effects, and the presence of functional groups can influence whether a compound can be synthesized via this method. Recognizing which substrates are suitable is essential for determining the feasibility of the reaction.

Functional Group Tolerance

Functional group tolerance in the Heck reaction pertains to the ability of the reaction to proceed in the presence of various functional groups on the substrates. Some functional groups can interfere with the reaction or may not survive the reaction conditions, thus limiting the types of compounds that can be synthesized. Understanding which functional groups are compatible is vital for predicting the outcome of the reaction.