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

35. Transition Metals

Catalytic Allylic Alkylation

Organic Chemistry

35. Transition Metals

Catalytic Allylic Alkylation

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Multiple Choice

Determine the product from the following catalytic allylic alkylation reaction.

Product of the catalytic allylic alkylation reaction with two cyano groups.

Product of the catalytic allylic alkylation reaction with one cyano group and a double bond.

Product of the catalytic allylic alkylation reaction with a cyano group and a branched structure.

Product of the catalytic allylic alkylation reaction with a cyano group and a different branched structure.

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Verified step by step guidance

Identify the reactants and the catalyst: The starting material is an allylic bromide, and the catalyst is tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4). The nucleophile is malononitrile (NC-CH2-CN).

Understand the mechanism: The reaction is a catalytic allylic alkylation, which involves the formation of a π-allyl palladium complex. The palladium catalyst facilitates the substitution of the bromide with the nucleophile.

Formation of the π-allyl palladium complex: The palladium catalyst coordinates with the allylic bromide, displacing the bromide ion and forming a π-allyl palladium intermediate.

Nucleophilic attack: The malononitrile anion, generated from deprotonation of malononitrile, attacks the less hindered carbon of the π-allyl palladium complex, leading to the formation of a new carbon-carbon bond.

Consider stereochemistry: The nucleophilic attack can occur from either face of the π-allyl complex, potentially leading to different stereoisomers. Analyze the possible stereochemical outcomes to determine the correct product.