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:
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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**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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