5. Provide a mechanism for the following transformation: H2SO4 ÓH

Chemistry
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Chapter1: Chemical Foundations
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**Question 5:** 

**Provide a mechanism for the following transformation:**

- The reactant is a tertiary alcohol, 2-methylpropan-2-ol.
- It undergoes a transformation in the presence of sulfuric acid (\( \text{H}_2\text{SO}_4 \)).

**Reaction Details:**
- **Reactant:** The molecule has a hydroxyl group (\( -\text{OH} \)) attached to the central carbon of a three-carbon chain with a methyl group attached to the second carbon.
  
- **Reagent:** \( \text{H}_2\text{SO}_4 \), which acts as a strong acid, indicating that the mechanism likely involves protonation.

- **Product:** The product is an alkene, specifically 2-methylpropene, formed by the elimination of water.

**Mechanism Explanation:**
1. **Protonation Step:** The hydroxyl group in the alcohol is protonated by the sulfuric acid. This step converts the \( -\text{OH} \) group into water (\( \text{H}_2\text{O} \)), a better leaving group.

2. **Formation of Carbocation:** Once the \( \text{H}_2\text{O} \) group leaves, a carbocation is formed at the tertiary carbon center.

3. **Deprotonation and Alkene Formation:** A hydrogen ion is abstracted from one of the neighboring carbon atoms, leading to the formation of a double bond between the carbons, resulting in the alkene.

This is an example of an acid-catalyzed dehydration reaction, which proceeds via an E1 mechanism typical in such transformations involving secondary or tertiary alcohols.
Transcribed Image Text:**Question 5:** **Provide a mechanism for the following transformation:** - The reactant is a tertiary alcohol, 2-methylpropan-2-ol. - It undergoes a transformation in the presence of sulfuric acid (\( \text{H}_2\text{SO}_4 \)). **Reaction Details:** - **Reactant:** The molecule has a hydroxyl group (\( -\text{OH} \)) attached to the central carbon of a three-carbon chain with a methyl group attached to the second carbon. - **Reagent:** \( \text{H}_2\text{SO}_4 \), which acts as a strong acid, indicating that the mechanism likely involves protonation. - **Product:** The product is an alkene, specifically 2-methylpropene, formed by the elimination of water. **Mechanism Explanation:** 1. **Protonation Step:** The hydroxyl group in the alcohol is protonated by the sulfuric acid. This step converts the \( -\text{OH} \) group into water (\( \text{H}_2\text{O} \)), a better leaving group. 2. **Formation of Carbocation:** Once the \( \text{H}_2\text{O} \) group leaves, a carbocation is formed at the tertiary carbon center. 3. **Deprotonation and Alkene Formation:** A hydrogen ion is abstracted from one of the neighboring carbon atoms, leading to the formation of a double bond between the carbons, resulting in the alkene. This is an example of an acid-catalyzed dehydration reaction, which proceeds via an E1 mechanism typical in such transformations involving secondary or tertiary alcohols.
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