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Mechanism. Provide the complete mechanism for the reaction below. You must include appropriate arrows, intermediates, and formal charges. The ChemDraw template of this document is available on Carmen. KOH (catalytic) EtOH 78 °C

Mechanism. Provide the complete mechanism for the reaction below. You must include appropriate arrows, intermediates, and formal charges. The ChemDraw template of this document is available on Carmen. KOH (catalytic) EtOH 78 °C

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
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Please show the mechanism for the reaction
**Mechanism.** Provide the complete mechanism for the reaction below. You must include appropriate arrows, intermediates, and formal charges. The ChemDraw template of this document is available on Carmen. **Reaction Overview:** - **Reactants:** - Acetone (CH₃COCH₃) - Benzil (C₁₄H₁₀O₂) - **Reagents:** - Potassium hydroxide (KOH, catalytic) - Ethanol (EtOH) - Temperature: 78 °C **Product:** - The product is a large, fused bicyclic aromatic compound featuring a central five-membered ring with three phenyl groups attached. This is indicative of a reaction forming a bimolecular product such as a triphenylmethanol derivative or related compound. **Mechanism Details:** 1. **Initial Steps:** - KOH serves as the base, initiating the reaction by deprotonating acetone to form an enolate ion. - The enolate then performs a nucleophilic attack on the carbonyl carbon of benzil. 2. **Formation of Intermediates:** - This step results in the formation of an alkoxide intermediate linked to benzil. - Intramolecular rearrangements and additional formations may occur, setting up for further reactions leading to cyclization. 3. **Cyclization:** - As the reaction proceeds, cyclization will occur, forming the new central five-membered ring structure. - Further rearrangements or proton transfers will lead to the final product structure, including stabilization via aromaticity or other resonance forms. 4. **Final Product:** - The reaction culminates in the formation of a stable bicyclic product, featuring three benzene rings. **Diagram Explanation:** - The structural diagrams depict the transition from the starting materials to the final aromatic compound. - Arrows in the diagram would typically illustrate the movement of electrons through bond formations and rearrangements. - Formal charges, if any, would be indicated next to relevant atoms. This mechanism reflects typical steps in an aldol condensation followed by benzoin condensation and cyclization. Understanding these steps is crucial in mastering organic synthesis techniques.
Transcribed Image Text:**Mechanism.** Provide the complete mechanism for the reaction below. You must include appropriate arrows, intermediates, and formal charges. The ChemDraw template of this document is available on Carmen. **Reaction Overview:** - **Reactants:** - Acetone (CH₃COCH₃) - Benzil (C₁₄H₁₀O₂) - **Reagents:** - Potassium hydroxide (KOH, catalytic) - Ethanol (EtOH) - Temperature: 78 °C **Product:** - The product is a large, fused bicyclic aromatic compound featuring a central five-membered ring with three phenyl groups attached. This is indicative of a reaction forming a bimolecular product such as a triphenylmethanol derivative or related compound. **Mechanism Details:** 1. **Initial Steps:** - KOH serves as the base, initiating the reaction by deprotonating acetone to form an enolate ion. - The enolate then performs a nucleophilic attack on the carbonyl carbon of benzil. 2. **Formation of Intermediates:** - This step results in the formation of an alkoxide intermediate linked to benzil. - Intramolecular rearrangements and additional formations may occur, setting up for further reactions leading to cyclization. 3. **Cyclization:** - As the reaction proceeds, cyclization will occur, forming the new central five-membered ring structure. - Further rearrangements or proton transfers will lead to the final product structure, including stabilization via aromaticity or other resonance forms. 4. **Final Product:** - The reaction culminates in the formation of a stable bicyclic product, featuring three benzene rings. **Diagram Explanation:** - The structural diagrams depict the transition from the starting materials to the final aromatic compound. - Arrows in the diagram would typically illustrate the movement of electrons through bond formations and rearrangements. - Formal charges, if any, would be indicated next to relevant atoms. This mechanism reflects typical steps in an aldol condensation followed by benzoin condensation and cyclization. Understanding these steps is crucial in mastering organic synthesis techniques.
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