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3. A student performed the following reaction and obtained a product with a chemical formula of C6H12O. Use the chemical formula and 'H NMR spectrum to determine the structure of the product. (No peaks exchange with D20). Then propose a mechanism for the reaction. H* / H,0 он но singlet |= 6 triplet |= 2 quintet |= 2 triplet | = 2 3.0 1.0 2.0 8 (ppm) 4.0 0.0 Mechanism:

3. A student performed the following reaction and obtained a product with a chemical formula of C6H12O. Use the chemical formula and 'H NMR spectrum to determine the structure of the product. (No peaks exchange with D20). Then propose a mechanism for the reaction. H* / H,0 он но singlet |= 6 triplet |= 2 quintet |= 2 triplet | = 2 3.0 1.0 2.0 8 (ppm) 4.0 0.0 Mechanism:

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ISBN:9781305957404
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Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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### Transcription for Educational Website **Reaction and Analysis:** A student performed a reaction yielding a product with the chemical formula C₆H₁₂O. Using the given chemical formula and the provided ¹H NMR spectrum, the task is to determine the structure of the product. Note that no peaks exchange with D₂O were observed. Following the analysis, a mechanism for the reaction is required. **Reaction Scheme:** The starting molecule is 1,2-hexanediol. Under acidic conditions (H⁺/H₂O), an unknown product is formed. **¹H NMR Spectrum Analysis:** The ¹H NMR spectrum includes the following signals: - **Triplet** at approximately 3.5 ppm with an integration (I) of 2, suggesting a CH₂ group adjacent to a heteroatom (e.g., oxygen). - **Quintet** at approximately 1.8 ppm with an integration (I) of 2, indicating a CH₂ group possibly adjacent to other CH₂ groups. - **Triplet** at approximately 1.2 ppm with an integration (I) of 2, suggesting another CH₂ group in a similar environment. - **Singlet** at approximately 1.1 ppm with a high integration (I) of 6, indicating two equivalent CH₃ groups. **Proposed Structure:** Based on the NMR data, the proposed structure could be a cyclic ether with six carbons, likely forming a tetrahydropyran derivative. **Mechanism:** The mechanism involves: 1. **Protonation** of the hydroxyl group, making it a better leaving group. 2. **Intramolecular Nucleophilic Attack** by the other hydroxyl group, leading to ring closure. 3. **Loss of Water** to form the cyclic ether: a six-membered tetrahydropyran ring. This analysis and mechanism provide a comprehensive approach to deducing the structure and formation process of the product from the given reaction and spectral data.
Transcribed Image Text:### Transcription for Educational Website **Reaction and Analysis:** A student performed a reaction yielding a product with the chemical formula C₆H₁₂O. Using the given chemical formula and the provided ¹H NMR spectrum, the task is to determine the structure of the product. Note that no peaks exchange with D₂O were observed. Following the analysis, a mechanism for the reaction is required. **Reaction Scheme:** The starting molecule is 1,2-hexanediol. Under acidic conditions (H⁺/H₂O), an unknown product is formed. **¹H NMR Spectrum Analysis:** The ¹H NMR spectrum includes the following signals: - **Triplet** at approximately 3.5 ppm with an integration (I) of 2, suggesting a CH₂ group adjacent to a heteroatom (e.g., oxygen). - **Quintet** at approximately 1.8 ppm with an integration (I) of 2, indicating a CH₂ group possibly adjacent to other CH₂ groups. - **Triplet** at approximately 1.2 ppm with an integration (I) of 2, suggesting another CH₂ group in a similar environment. - **Singlet** at approximately 1.1 ppm with a high integration (I) of 6, indicating two equivalent CH₃ groups. **Proposed Structure:** Based on the NMR data, the proposed structure could be a cyclic ether with six carbons, likely forming a tetrahydropyran derivative. **Mechanism:** The mechanism involves: 1. **Protonation** of the hydroxyl group, making it a better leaving group. 2. **Intramolecular Nucleophilic Attack** by the other hydroxyl group, leading to ring closure. 3. **Loss of Water** to form the cyclic ether: a six-membered tetrahydropyran ring. This analysis and mechanism provide a comprehensive approach to deducing the structure and formation process of the product from the given reaction and spectral data.
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