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

Sonogashira Coupling Reaction

Organic Chemistry

35. Transition Metals

Sonogashira Coupling Reaction

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3:47 minutes

Problem 29

Textbook Question

The coupling of an alkyne with an aryl halide in the presence of a palladium catalyst and triethylamine is called a Sonogashira reaction. What reactants couple to form this product?

Verified step by step guidance

Step 1: Recognize that the Sonogashira reaction involves the coupling of an alkyne with an aryl halide in the presence of a palladium catalyst and a base such as triethylamine.

Step 2: Analyze the product structure provided in the image. The product contains a phenyl group (benzene ring) attached to a terminal alkyne group with an ethyl substituent.

Step 3: Identify the two reactants required for the Sonogashira reaction. The phenyl group suggests the use of an aryl halide, such as bromobenzene or iodobenzene. The terminal alkyne group with an ethyl substituent suggests the use of ethynylbenzene (C≡C-CH2CH3).

Step 4: Write the general reaction scheme for the Sonogashira reaction: Ar-X + R-C≡CH → Ar-C≡C-R, where Ar-X is the aryl halide and R-C≡CH is the terminal alkyne.

Step 5: Confirm that the reactants bromobenzene (or iodobenzene) and ethynylbenzene (C≡C-CH2CH3) would couple under Sonogashira reaction conditions to form the product shown in the image.

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Key Concepts

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

Sonogashira Reaction

The Sonogashira reaction is a cross-coupling reaction that involves the coupling of an alkyne with an aryl halide using a palladium catalyst and a base, typically triethylamine. This reaction is significant in organic synthesis for forming carbon-carbon bonds, particularly in the construction of complex molecules and materials.

Palladium Catalysis

Palladium is a transition metal that serves as a catalyst in various organic reactions, including the Sonogashira reaction. Its ability to facilitate the formation and breaking of carbon-carbon bonds makes it essential for promoting the coupling of alkynes and aryl halides, enhancing reaction rates and selectivity.

Aryl Halides

Aryl halides are organic compounds that contain a halogen atom (such as chlorine, bromine, or iodine) bonded to an aromatic ring. In the context of the Sonogashira reaction, these compounds act as electrophiles, reacting with nucleophilic alkynes to form new carbon-carbon bonds, which are crucial for synthesizing more complex organic structures.

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Related Practice

Textbook Question

Suggest two coupling partners that could be used to synthesize the compounds shown making the indicated C―C bonds.

(a)

Textbook Question

The trimethylsilyl (TMS) group, used as a protecting group for alcohols, can also be used a protecting group for terminal alkynes. Show how TMS-acetylene could be used to link together two aryl halides using the Sonogashira reaction. [Hint: Deprotection of the TMS-acetylene can be done using KF in H₂O.]

Open Question

Determine the product from the following Sonogashira Reaction.

Open Question

Determine compounds A, B, and C from the following reaction sequence.

Textbook Question

Predict the product of the following Sonogashira coupling reactions.

(a)

Textbook Question

Predict the product of the following Sonogashira coupling reactions.

(b)

Textbook Question

Suggest two coupling partners that could be used to synthesize the compounds shown making the indicated C―C bonds.