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

9. Alkenes and Alkynes

Hydrogenation of Alkynes

Organic Chemistry

9. Alkenes and Alkynes

Hydrogenation of Alkynes

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4:28 minutes

Problem 7.19

Textbook Question

The following reaction was recently reported to have been performed electrochemically.

(a) Identify the reagent and a solvent that could have been used if this reaction was done traditionally.
(b) What safety and environmental hazards are improved or worsened when doing this reaction electrochemically?

Verified step by step guidance

Step 1: Analyze the reaction provided in the image. The reaction involves the coupling of a terminal alkyne (phenylacetylene) to form a biphenyl structure. The reaction uses PdCl₂ (2 mol%) as a catalyst, (CH₃)₂NH (0.5 mol equiv.) as a base, Bu₄NI (1 mol equiv.) as an additive, and CH₃OH as the solvent at 60°C.

Step 2: For part (a), identify the reagent and solvent that could be used traditionally. Traditionally, this reaction could be performed using a palladium catalyst (e.g., Pd(PPh₃)₄) and a base such as triethylamine (Et₃N) or potassium carbonate (K₂CO₃). A common solvent for such reactions could be tetrahydrofuran (THF) or dimethylformamide (DMF).

Step 3: For part (b), consider the safety and environmental hazards of performing the reaction electrochemically versus traditionally. Electrochemical methods can reduce the need for toxic reagents (e.g., strong bases or oxidants) and may generate fewer hazardous byproducts. However, electrochemical setups require specialized equipment and may involve electrical hazards.

Step 4: Compare the environmental impact. Electrochemical reactions often have a lower carbon footprint and can be more sustainable, as they may avoid the use of volatile organic solvents or heavy metals. However, traditional methods may be simpler to scale up and require less energy input.

Step 5: Summarize the advantages and disadvantages. Electrochemical methods improve safety by reducing exposure to toxic chemicals and environmental hazards but may introduce challenges related to equipment and energy use. Traditional methods may be more straightforward but could involve greater environmental risks due to the use of hazardous reagents and solvents.

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Key Concepts

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

Electrochemical Reactions

Electrochemical reactions involve the transfer of electrons between chemical species, often facilitated by an external electrical current. These reactions can be used to drive transformations that may not occur under standard conditions. Understanding the principles of oxidation and reduction is crucial, as they dictate the flow of electrons and the overall reaction mechanism.

Reagents and Solvents in Organic Reactions

In organic chemistry, reagents are substances that participate in a chemical reaction, while solvents are the mediums in which reactions occur. The choice of reagent and solvent can significantly influence the reaction's efficiency, selectivity, and yield. For traditional reactions, common solvents include water, alcohols, or organic solvents, which can affect the reaction's environmental impact and safety.

Safety and Environmental Hazards

Safety and environmental hazards in chemical reactions refer to the potential risks associated with the materials and processes used. Electrochemical methods can reduce certain hazards by minimizing the use of toxic reagents and solvents, but they may introduce new risks, such as electrical hazards or the production of hazardous byproducts. Evaluating these factors is essential for sustainable chemistry practices.

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