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

Previous problemNext problem

3:27 minutes

Problem 11aBruice - 8th Edition

Textbook Question

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

Verified step by step guidance

Identify the type of reaction: This is a Heck reaction, which involves the coupling of an aryl halide with an alkene in the presence of a palladium catalyst.

Determine the reactants: The reactants are iodobenzene (C6H5I) and acrylonitrile (CH2=CH-CN).

Understand the role of the catalyst: The palladium catalyst (L2Pd) and the base (triethylamine, (CH3CH2)3N) facilitate the coupling reaction.

Predict the product: The Heck reaction typically results in the formation of a new carbon-carbon bond between the aryl group and the alkene, with the double bond shifting to accommodate the new bond.

Draw the product: The product will be a substituted alkene where the phenyl group (C6H5) is attached to the carbon of the acrylonitrile that was originally part of the double bond, resulting in C6H5-CH=CH-CN.

Recommended similar problem, with video answer:

Verified Solution

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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 halide and an alkene, resulting in the formation of a substituted alkene. This reaction is significant in organic synthesis for creating carbon-carbon bonds and is widely used in the pharmaceutical and materials industries. The reaction typically requires a base and a ligand to stabilize the palladium catalyst.

Palladium Catalysis

Palladium catalysis involves the use of palladium compounds as catalysts in various organic reactions, including cross-coupling reactions like the Heck reaction. Palladium's ability to facilitate the formation and breaking of carbon-carbon bonds makes it a valuable tool in synthetic organic chemistry. The choice of ligands and reaction conditions can significantly influence the efficiency and selectivity of the reaction.

Aryl Halides

Aryl halides are organic compounds containing a halogen atom bonded to an aromatic ring. They are important substrates in many organic reactions, including the Heck reaction, where they serve as the electrophilic partner. The reactivity of aryl halides can vary based on the nature of the halogen and the substituents on the aromatic ring, affecting the overall reaction outcome.