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6. Propose a reasonable mechanism, using curved arrow notation, for the following transformation. You may use only the reagents provided. H* H₂O HO OH

6. Propose a reasonable mechanism, using curved arrow notation, for the following transformation. You may use only the reagents provided. H* H₂O HO OH

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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### Question 6 Propose a reasonable mechanism, using curved arrow notation, for the following transformation. You may use only the reagents provided. ### Transformation Description - **Starting Material**: A molecule with a tert-butyl group attached to two double-bonded adjacent carbon atoms, connected to a linear chain of five carbon atoms. - **Reagents**: Acid (H⁺) and Water (H₂O) - **Product**: A diol with two cyclohexane rings bonded to a carbon atom which is also bonded to a tert-butyl group. ### Detailed Description of Reaction 1. **Acid-Catalyzed Addition**: In the presence of an acid, the double bonds are activated for a nucleophilic attack. 2. **Nucleophilic Attack by Water**: Water adds across the activated π-bonds. 3. **Hydration and Ring Formation**: The molecule undergoes cyclization to form the six-membered rings. 4. **Formation of Diol**: The final product is a diol with the hydroxyl groups positioned on the cyclohexane rings. ### Molecular Structures - **Starting Material**: Contains a six-carbon linear chain with two double bonds starting from the second carbon, terminating with a tert-butyl group. - **End Product**: A diol featuring two connected cyclohexane rings, with hydroxyl groups on each ring, and a tert-butyl group attached to the connecting carbon. ### Detailed Mechanism Steps 1. Protonation of the double bonds causes a carbocation formation. 2. Intramolecular attack leads to the closure of the rings. 3. Hydration of the carbocations forms the hydroxyl groups on the newly formed cyclohexane rings. For further detailed mechanisms and curved arrow notation, refer to standard organic chemistry textbooks on electrophilic addition and ring formation reactions.
Transcribed Image Text:### Question 6 Propose a reasonable mechanism, using curved arrow notation, for the following transformation. You may use only the reagents provided. ### Transformation Description - **Starting Material**: A molecule with a tert-butyl group attached to two double-bonded adjacent carbon atoms, connected to a linear chain of five carbon atoms. - **Reagents**: Acid (H⁺) and Water (H₂O) - **Product**: A diol with two cyclohexane rings bonded to a carbon atom which is also bonded to a tert-butyl group. ### Detailed Description of Reaction 1. **Acid-Catalyzed Addition**: In the presence of an acid, the double bonds are activated for a nucleophilic attack. 2. **Nucleophilic Attack by Water**: Water adds across the activated π-bonds. 3. **Hydration and Ring Formation**: The molecule undergoes cyclization to form the six-membered rings. 4. **Formation of Diol**: The final product is a diol with the hydroxyl groups positioned on the cyclohexane rings. ### Molecular Structures - **Starting Material**: Contains a six-carbon linear chain with two double bonds starting from the second carbon, terminating with a tert-butyl group. - **End Product**: A diol featuring two connected cyclohexane rings, with hydroxyl groups on each ring, and a tert-butyl group attached to the connecting carbon. ### Detailed Mechanism Steps 1. Protonation of the double bonds causes a carbocation formation. 2. Intramolecular attack leads to the closure of the rings. 3. Hydration of the carbocations forms the hydroxyl groups on the newly formed cyclohexane rings. For further detailed mechanisms and curved arrow notation, refer to standard organic chemistry textbooks on electrophilic addition and ring formation reactions.
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