Provide a mechanism for the following transformation, clearly illustrating each step with curved arrows. CH3 conc. H₂SO4 A CH3

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**Title: Mechanism for the Acid-Catalyzed Transformation of Methyloxacyclohexane to Methylbenzene**

**Objective:** 
To provide a detailed mechanism of methyloxacyclohexane conversion into methylbenzene using concentrated sulfuric acid (H₂SO₄) with heating (Δ).

**Chemical Reaction:**
- Starting Material: Methyloxacyclohexane
- Reagent: Concentrated H₂SO₄
- Product: Methylbenzene
- Conditions: Heat (Δ)

**Reaction Mechanism:**

1. **Protonation of the Ether Oxygen:**
   - The reaction begins with the protonation of the oxygen atom in the methyloxacyclohexane by concentrated sulfuric acid. This step generates a good leaving group, allowing the ring to open.

2. **Formation of a Carbocation:**
   - The protonated intermediate loses a water molecule, resulting in the formation of a carbocation. The stability of this carbocation is critical for the subsequent rearrangement.

3. **Rearrangement and Ring Expansion:**
   - The carbocation undergoes a 1,2-hydride or alkyl shift to form a more stable carbocation. This step is crucial as it facilitates the rearrangement necessary for the formation of the aromatic ring.

4. **Deprotonation:**
   - The final step involves deprotonation, leading to the formation of an aromatic compound. In this case, the newly formed carbocation loses a proton to yield methylbenzene.

**Diagram Explanation:**

The diagram shows:
- A methyloxacyclohexane with a wedge indicating the methyl group orientation.
- An arrow pointing towards the right, labeled with "conc. H₂SO₄" and a delta symbol (Δ) indicates heating.
- The product, methylbenzene, shown with the methyl group and aromatic ring.

**Conclusion:**

The transformation from methyloxacyclohexane to methylbenzene involves protonation, ring opening, carbocation rearrangement, and subsequent formation of the aromatic ring through deprotonation. Each step should be carefully analyzed, emphasizing the role of concentrated sulfuric acid and heating in facilitating the rearrangement and elimination processes leading to the formation of aromatic compounds.
Transcribed Image Text:**Title: Mechanism for the Acid-Catalyzed Transformation of Methyloxacyclohexane to Methylbenzene** **Objective:** To provide a detailed mechanism of methyloxacyclohexane conversion into methylbenzene using concentrated sulfuric acid (H₂SO₄) with heating (Δ). **Chemical Reaction:** - Starting Material: Methyloxacyclohexane - Reagent: Concentrated H₂SO₄ - Product: Methylbenzene - Conditions: Heat (Δ) **Reaction Mechanism:** 1. **Protonation of the Ether Oxygen:** - The reaction begins with the protonation of the oxygen atom in the methyloxacyclohexane by concentrated sulfuric acid. This step generates a good leaving group, allowing the ring to open. 2. **Formation of a Carbocation:** - The protonated intermediate loses a water molecule, resulting in the formation of a carbocation. The stability of this carbocation is critical for the subsequent rearrangement. 3. **Rearrangement and Ring Expansion:** - The carbocation undergoes a 1,2-hydride or alkyl shift to form a more stable carbocation. This step is crucial as it facilitates the rearrangement necessary for the formation of the aromatic ring. 4. **Deprotonation:** - The final step involves deprotonation, leading to the formation of an aromatic compound. In this case, the newly formed carbocation loses a proton to yield methylbenzene. **Diagram Explanation:** The diagram shows: - A methyloxacyclohexane with a wedge indicating the methyl group orientation. - An arrow pointing towards the right, labeled with "conc. H₂SO₄" and a delta symbol (Δ) indicates heating. - The product, methylbenzene, shown with the methyl group and aromatic ring. **Conclusion:** The transformation from methyloxacyclohexane to methylbenzene involves protonation, ring opening, carbocation rearrangement, and subsequent formation of the aromatic ring through deprotonation. Each step should be carefully analyzed, emphasizing the role of concentrated sulfuric acid and heating in facilitating the rearrangement and elimination processes leading to the formation of aromatic compounds.
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