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

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Chapter1: Chemical Foundations
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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.
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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