5. Draw a plausible mechanism for the following reaction. For full credit, show all intermediates, formal charges, lone pairs of electrons, and relevant stereochemistry. H₂O OH Ni
5. Draw a plausible mechanism for the following reaction. For full credit, show all intermediates, formal charges, lone pairs of electrons, and relevant stereochemistry. H₂O OH Ni
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 5
**Description:**
Draw a plausible mechanism for the following reaction. For full credit, show all intermediates, formal charges, lone pairs of electrons, and relevant stereochemistry.
**Explanation:**
The reaction displayed involves a tertiary alkyl chloride (left-hand structure) reacting with water (H₂O) to form a tertiary alcohol (right-hand structure).
- **Starting Material:** A tertiary alkyl chloride with an N-atom bonded to the carbon adjacent to the chlorinated carbon.
- **Reagent:** Water (H₂O)
- **Product:** A tertiary alcohol with similar connectivity but with a hydroxyl (OH) group replacing the chlorine atom.
**Instructions:**
1. **Initiate the reaction** by showing the departure of the chloride ion, forming a carbocation at the same location.
2. **Hydration of the carbocation** occurs when the lone pair of electrons on the oxygen of the water molecule attacks the carbocation, leading to the formation of a protonated alcohol intermediate.
3. Finally, **deprotonation** of the protonated intermediate yields the neutral alcohol product.
Throughout the reaction, users should illustrate the placement of lone pairs of electrons, formal charges, and the stereochemistry retained throughout the process.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F06f0fbe0-f317-435d-a2b5-90be2d5876f1%2Fcfa845d4-34fe-4a6b-b0a9-66ce6abe4d8c%2Fse9vlcj_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Question 5
**Description:**
Draw a plausible mechanism for the following reaction. For full credit, show all intermediates, formal charges, lone pairs of electrons, and relevant stereochemistry.
**Explanation:**
The reaction displayed involves a tertiary alkyl chloride (left-hand structure) reacting with water (H₂O) to form a tertiary alcohol (right-hand structure).
- **Starting Material:** A tertiary alkyl chloride with an N-atom bonded to the carbon adjacent to the chlorinated carbon.
- **Reagent:** Water (H₂O)
- **Product:** A tertiary alcohol with similar connectivity but with a hydroxyl (OH) group replacing the chlorine atom.
**Instructions:**
1. **Initiate the reaction** by showing the departure of the chloride ion, forming a carbocation at the same location.
2. **Hydration of the carbocation** occurs when the lone pair of electrons on the oxygen of the water molecule attacks the carbocation, leading to the formation of a protonated alcohol intermediate.
3. Finally, **deprotonation** of the protonated intermediate yields the neutral alcohol product.
Throughout the reaction, users should illustrate the placement of lone pairs of electrons, formal charges, and the stereochemistry retained throughout the process.
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