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

Stille Reaction

Organic Chemistry

35. Transition Metals

Stille Reaction

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2:26 minutes

Problem 16a

Textbook Question

The Stille reaction is similar to the Suzuki reaction. It replaces the alkenyl-organoboron compound of the Suzuki reaction with an alkenyl-organotin compound. (R is an alkyl group such as methyl or butyl.) Unlike the alkenyl-organoboron compound that always has a trans configuration, the alkenyl-organotin compound can have a cis configuration. What is the product of the Stille reaction shown here?

Verified step by step guidance

Step 1: Recognize the reaction type. The Stille reaction is a palladium-catalyzed cross-coupling reaction between an organohalide (in this case, a bromide) and an organotin compound. The goal is to form a new carbon-carbon bond between the two reactants.

Step 2: Analyze the reactants. The organohalide is a cyclohexenyl bromide, which contains a double bond in the cyclohexene ring. The organotin compound is an alkenyl-organotin species, specifically a vinyl group attached to tin (Sn(R)3).

Step 3: Understand the mechanism. The palladium catalyst (L2Pd) facilitates the oxidative addition of the bromide to palladium, forming a Pd(II) complex. This is followed by transmetalation, where the alkenyl group from the organotin compound is transferred to the palladium complex.

Step 4: Consider the stereochemistry. The alkenyl-organotin compound can have cis or trans configurations. The stereochemistry of the product depends on the configuration of the alkenyl-organotin compound used in the reaction.

Step 5: Predict the product. The final step in the Stille reaction is reductive elimination, where the alkenyl group from the organotin compound and the cyclohexenyl group from the organohalide combine to form a new carbon-carbon double bond. The product will be a conjugated diene, specifically 1-vinylcyclohexene.

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Key Concepts

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

Stille Reaction

The Stille reaction is a cross-coupling reaction that involves the coupling of an organotin compound with an organic halide in the presence of a palladium catalyst. This reaction is particularly useful for forming carbon-carbon bonds and is widely applied in organic synthesis. The ability of organotin compounds to participate in this reaction allows for the introduction of various alkenyl groups into organic molecules.

Organotin Compounds

Organotin compounds are organometallic compounds that contain tin bonded to carbon. They are often used in the Stille reaction due to their stability and reactivity. Unlike organoboron compounds, organotin compounds can exist in both cis and trans configurations, which can influence the stereochemistry of the final product in reactions where stereochemistry is critical.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of the Stille reaction, the configuration of the alkenyl-organotin compound (cis or trans) can lead to different stereoisomers in the product. Understanding stereochemistry is essential for predicting the properties and reactivity of the resulting compounds.

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