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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Which compound is
![**Title: Identification of the Compound with the Greatest Number of \(^{13}\)C-NMR Signals**
In the image, four organic compounds are depicted, each with distinct structural characteristics. The task is to determine which compound will exhibit the greatest number of distinct \(^{13}\)C-Nuclear Magnetic Resonance (NMR) signals. \(^{13}\)C-NMR spectroscopy is an essential tool in organic chemistry for understanding the carbon skeleton of a molecule, as each unique carbon environment yields a separate signal.
**Description of Compounds:**
1. **Compound 1:** This structure features a cyclopentanone (five-membered ring with a carbonyl group) attached to a cyclopentyl group. The presence of the carbonyl functional group could potentially lead to distinct signals due to deshielding effects.
2. **Compound 2:** This molecule consists of two cyclopentane rings connected by a single bond. It's symmetrical, which might limit the number of unique carbon environments.
3. **Compound 3:** Similar to Compound 2, this structure is a bicyclic compound composed of two connected cyclopentane rings, but the connectivity allows for some asymmetry due to different spatial arrangements.
4. **Compound 4:** A bicyclo[2.2.1]heptane system, known for its symmetry. The mirror plane in this rigid system greatly reduces the number of unique carbon environments.
**Analysis:**
- **Compound 1** is likely to have the highest number of distinct \(^{13}\)C-NMR signals. The carbonyl group and the lack of symmetry compared to the other compounds lead to a greater number of unique carbon environments.
- **Compounds 2 and 3** are structurally similar, with some asymmetry in Compound 3 that might provide slightly more unique environments than Compound 2.
- **Compound 4** is expected to have fewer signals due to its high symmetry and the shared carbon environments in the bicyclic system.
In conclusion, analyzing symmetries and functional groups helps in predicting the number of \(^{13}\)C-NMR signals a compound might exhibit, making Compound 1 the prime candidate for having the greatest number of signals.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F2d95edf5-a7eb-463b-b7f4-ca02808af034%2Ffa9fb4ce-ef68-4840-9255-d7f40fc7ee3a%2F101m9kk_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Title: Identification of the Compound with the Greatest Number of \(^{13}\)C-NMR Signals**
In the image, four organic compounds are depicted, each with distinct structural characteristics. The task is to determine which compound will exhibit the greatest number of distinct \(^{13}\)C-Nuclear Magnetic Resonance (NMR) signals. \(^{13}\)C-NMR spectroscopy is an essential tool in organic chemistry for understanding the carbon skeleton of a molecule, as each unique carbon environment yields a separate signal.
**Description of Compounds:**
1. **Compound 1:** This structure features a cyclopentanone (five-membered ring with a carbonyl group) attached to a cyclopentyl group. The presence of the carbonyl functional group could potentially lead to distinct signals due to deshielding effects.
2. **Compound 2:** This molecule consists of two cyclopentane rings connected by a single bond. It's symmetrical, which might limit the number of unique carbon environments.
3. **Compound 3:** Similar to Compound 2, this structure is a bicyclic compound composed of two connected cyclopentane rings, but the connectivity allows for some asymmetry due to different spatial arrangements.
4. **Compound 4:** A bicyclo[2.2.1]heptane system, known for its symmetry. The mirror plane in this rigid system greatly reduces the number of unique carbon environments.
**Analysis:**
- **Compound 1** is likely to have the highest number of distinct \(^{13}\)C-NMR signals. The carbonyl group and the lack of symmetry compared to the other compounds lead to a greater number of unique carbon environments.
- **Compounds 2 and 3** are structurally similar, with some asymmetry in Compound 3 that might provide slightly more unique environments than Compound 2.
- **Compound 4** is expected to have fewer signals due to its high symmetry and the shared carbon environments in the bicyclic system.
In conclusion, analyzing symmetries and functional groups helps in predicting the number of \(^{13}\)C-NMR signals a compound might exhibit, making Compound 1 the prime candidate for having the greatest number of signals.
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