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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Concept explainers
Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
Question
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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