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a. b. Propose a mechanism and final product for the following reactions. SiMe3 PhB(OH)2 cat. Pd(PPH3)4 Na₂CO3 S Ph CO₂Et cat. Pd(OAc)2 K₂CO3, Bu4N+ I¯ C13H16SSi -C15H140₂S

a. b. Propose a mechanism and final product for the following reactions. SiMe3 PhB(OH)2 cat. Pd(PPH3)4 Na₂CO3 S Ph CO₂Et cat. Pd(OAc)2 K₂CO3, Bu4N+ I¯ C13H16SSi -C15H140₂S

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Title: Propose a Mechanism and Final Product for Reactions** Below are two chemical reactions for which a mechanism and final product are to be proposed. --- **Reaction a:** **Substrates:** - A trimethylsilyl-substituted five-membered aromatic ring with an iodine substituent (R1). - Phenylboronic acid (PhB(OH)₂). **Catalyst:** - Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄). **Base:** - Sodium carbonate (Na₂CO₃). **Final Product:** - A compound with the molecular formula C₁₃H₁₆SSi. **Reaction b:** **Substrates:** - A five-membered aromatic ring with a phenyl and an iodine substituent (R2). - Ethyl acrylate (Vinyl group bonded to CO₂Et). **Catalyst:** - Palladium(II) acetate (Pd(OAc)₂). **Base:** - Potassium carbonate (K₂CO₃). **Additive:** - Tetrabutylammonium iodide (Bu₄N⁺ I⁻). **Final Product:** - A compound with the molecular formula C₁₅H₁₄O₂S. --- These reactions are set in an organometallic framework and require careful consideration of the catalyst and base used to achieve the desired transformation. They demonstrate the application of cross-coupling methodologies involving palladium catalysis.
Transcribed Image Text:**Title: Propose a Mechanism and Final Product for Reactions** Below are two chemical reactions for which a mechanism and final product are to be proposed. --- **Reaction a:** **Substrates:** - A trimethylsilyl-substituted five-membered aromatic ring with an iodine substituent (R1). - Phenylboronic acid (PhB(OH)₂). **Catalyst:** - Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄). **Base:** - Sodium carbonate (Na₂CO₃). **Final Product:** - A compound with the molecular formula C₁₃H₁₆SSi. **Reaction b:** **Substrates:** - A five-membered aromatic ring with a phenyl and an iodine substituent (R2). - Ethyl acrylate (Vinyl group bonded to CO₂Et). **Catalyst:** - Palladium(II) acetate (Pd(OAc)₂). **Base:** - Potassium carbonate (K₂CO₃). **Additive:** - Tetrabutylammonium iodide (Bu₄N⁺ I⁻). **Final Product:** - A compound with the molecular formula C₁₅H₁₄O₂S. --- These reactions are set in an organometallic framework and require careful consideration of the catalyst and base used to achieve the desired transformation. They demonstrate the application of cross-coupling methodologies involving palladium catalysis.
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