Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL4: Proton (1h) Nmr Spectroscopy
Section: Chapter Questions
Problem 4CTQ
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![**Determining the Matching Structure Based on ^1H-NMR Spectrum**
**Question:**
Which structure best matches the ^1H-NMR spectrum below?
**Explanation of the ^1H-NMR Spectrum:**
- The ^1H-NMR spectrum presented shows various peaks corresponding to the hydrogen atoms in the molecule under examination.
- **Peak Identification:**
- A multiplet (several overlapping peaks) near 7.5 - 8.0 PPM indicates the presence of aromatic hydrogen atoms.
- A singlet at approximately 5.5 PPM suggests the presence of a hydrogen atom in a less shielded environment.
**Structures Available for Matching:**
1. **Structure a:**
- Benzene ring with two hydroxyl (OH) groups attached.
2. **Structure b:**
- Benzene ring with a nitro (NO₂) group and an amino (NH₂) group attached.
3. **Structure c:**
- Benzene ring with two hydroxyl (OH) groups attached in meta positions.
4. **Structure d:**
- Benzene ring with a nitro (NO₂) group and an amino (NH₂) group attached in ortho positions.
5. **Structure e:**
- Benzene ring with two hydroxyl (OH) groups in ortho positions.
6. **Structure f:**
- Similar to structure d, it has a benzen ring with a nitro (NO₂) group and an amino (NH₂) group but not at the same positions.
**Analysis:**
- The aromatic region (7.0 - 8.0 PPM) signifies the hydrogens in an aromatic ring.
- The 5.5 PPM singlet may suggest a hydroxyl group on an aromatic ring.
**Conclusion:**
The best matching structure should show a similar pattern in its hydrogen environment as displayed in the NMR spectrum. Given the singlet at 5.5 PPM and multiplets in the aromatic region, the structure that is likely a match will have hydrogens in similar environments.
For educational purposes, matching ^1H-NMR spectra to structures is an excellent exercise in understanding hydrogen environments in various organic molecules.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fd556e803-222c-475e-bc6a-44d8250d1cd2%2F6cb1df0c-3d69-4785-9d76-2d6ac38eee24%2Fhhhsais_processed.png&w=3840&q=75)
Transcribed Image Text:**Determining the Matching Structure Based on ^1H-NMR Spectrum**
**Question:**
Which structure best matches the ^1H-NMR spectrum below?
**Explanation of the ^1H-NMR Spectrum:**
- The ^1H-NMR spectrum presented shows various peaks corresponding to the hydrogen atoms in the molecule under examination.
- **Peak Identification:**
- A multiplet (several overlapping peaks) near 7.5 - 8.0 PPM indicates the presence of aromatic hydrogen atoms.
- A singlet at approximately 5.5 PPM suggests the presence of a hydrogen atom in a less shielded environment.
**Structures Available for Matching:**
1. **Structure a:**
- Benzene ring with two hydroxyl (OH) groups attached.
2. **Structure b:**
- Benzene ring with a nitro (NO₂) group and an amino (NH₂) group attached.
3. **Structure c:**
- Benzene ring with two hydroxyl (OH) groups attached in meta positions.
4. **Structure d:**
- Benzene ring with a nitro (NO₂) group and an amino (NH₂) group attached in ortho positions.
5. **Structure e:**
- Benzene ring with two hydroxyl (OH) groups in ortho positions.
6. **Structure f:**
- Similar to structure d, it has a benzen ring with a nitro (NO₂) group and an amino (NH₂) group but not at the same positions.
**Analysis:**
- The aromatic region (7.0 - 8.0 PPM) signifies the hydrogens in an aromatic ring.
- The 5.5 PPM singlet may suggest a hydroxyl group on an aromatic ring.
**Conclusion:**
The best matching structure should show a similar pattern in its hydrogen environment as displayed in the NMR spectrum. Given the singlet at 5.5 PPM and multiplets in the aromatic region, the structure that is likely a match will have hydrogens in similar environments.
For educational purposes, matching ^1H-NMR spectra to structures is an excellent exercise in understanding hydrogen environments in various organic molecules.
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