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"ropose a mechanism for the following reaction. но H,SO, + H,0

"ropose a mechanism for the following reaction. но H,SO, + H,0

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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**Propose a Mechanism for the Following Reaction:** The reaction involves the hydration of an alkene in the presence of sulfuric acid. **Reactants:** - An alkene with a branched configuration (specifically a methyl propene derivative). - Water (H₂O). **Reagents:** - Sulfuric acid (H₂SO₄) is used as a catalyst. **Product:** - A tertiary alcohol, formed by the addition of a hydroxyl group (OH) to the more substituted carbon of the alkene. **Proposed Mechanism:** 1. **Protonation of the Alkene:** - The alkene undergoes protonation by the acid (H⁺ from H₂SO₄), resulting in the formation of a more stable carbocation. The proton is added to the less substituted carbon, following Markovnikov's rule, leading to a tertiary carbocation. 2. **Nucleophilic Attack by Water:** - Water acts as a nucleophile and attacks the carbocation, leading to the formation of an oxonium ion. 3. **Deprotonation:** - The oxonium ion loses a proton, resulting in the formation of the alcohol. The sulfuric acid is regenerated, allowing it to act as a catalyst. **Diagram Explanation:** - The left side of the diagram shows the alkene with the double bond that will react with water. - The arrow indicates the reaction proceeds with sulfuric acid as a catalyst. - The right side of the diagram shows the resulting alcohol, where the hydroxyl group is attached to the more substituted carbon, completing the reaction. This mechanism demonstrates a typical acid-catalyzed hydration of an alkene, showcasing the importance of carbocation stability and regioselectivity in the reaction.
Transcribed Image Text:**Propose a Mechanism for the Following Reaction:** The reaction involves the hydration of an alkene in the presence of sulfuric acid. **Reactants:** - An alkene with a branched configuration (specifically a methyl propene derivative). - Water (H₂O). **Reagents:** - Sulfuric acid (H₂SO₄) is used as a catalyst. **Product:** - A tertiary alcohol, formed by the addition of a hydroxyl group (OH) to the more substituted carbon of the alkene. **Proposed Mechanism:** 1. **Protonation of the Alkene:** - The alkene undergoes protonation by the acid (H⁺ from H₂SO₄), resulting in the formation of a more stable carbocation. The proton is added to the less substituted carbon, following Markovnikov's rule, leading to a tertiary carbocation. 2. **Nucleophilic Attack by Water:** - Water acts as a nucleophile and attacks the carbocation, leading to the formation of an oxonium ion. 3. **Deprotonation:** - The oxonium ion loses a proton, resulting in the formation of the alcohol. The sulfuric acid is regenerated, allowing it to act as a catalyst. **Diagram Explanation:** - The left side of the diagram shows the alkene with the double bond that will react with water. - The arrow indicates the reaction proceeds with sulfuric acid as a catalyst. - The right side of the diagram shows the resulting alcohol, where the hydroxyl group is attached to the more substituted carbon, completing the reaction. This mechanism demonstrates a typical acid-catalyzed hydration of an alkene, showcasing the importance of carbocation stability and regioselectivity in the reaction.
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