Chemistry
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Transcribed Image Text:**NMR and Infrared Spectral Analysis of C₅H₉NO₄**
**Question 2:**
The proton NMR spectrum is provided for a compound with the formula C₅H₉NO₄. The infrared (IR) spectrum presents prominent absorption bands at 1750 cm⁻¹ and 1562 cm⁻¹, along with a medium-intensity band at 1320 cm⁻¹. Detailed below are the findings from the normal carbon-13 NMR and DEPT (Distortionless Enhancement by Polarization Transfer) experiments. The task is to determine the structure of this compound based on this data.
**Carbon-13 and DEPT Results:**
| Normal Carbon | DEPT-135 | DEPT-90 |
|---------------|----------|-----------|
| 14 ppm | Positive | No peak |
| 16 ppm | Positive | No peak |
| 63 ppm | Negative | No peak |
| 83 ppm | Positive | Positive |
| 165 ppm | No peak | No peak |
**Proton NMR Spectrum:**
- The spectrum displays shifts at the following ppm values:
- 0.92 ppm
- 2.01 ppm
- 3.00 ppm
**Diagram Explanation:**
- The *Proton Spectrum* graph demonstrates peaks corresponding to different hydrogen environments within the molecule.
- The x-axis represents the chemical shift in parts per million (ppm), ranging from 5.0 to 0.0 ppm.
- The y-axis shows signal intensity.
- Notable peaks are observed at approximately 0.92, 2.01, and 3.00 ppm, indicating distinct proton environments.
**Structural Analysis:**
- **IR Spectroscopy:** The absorption bands at 1750 and 1562 cm⁻¹ suggest the presence of carbonyl (C=O) and possibly nitro (NO₂) groups.
- **NMR Data:** Analyzing shifts and DEPT results assists in identifying carbon environments:
- *14 and 16 ppm* (CH₃ groups as suggested by their positive signal in DEPT-135 and no signal in DEPT-90)
- *63 ppm* (likely an oxygenated carbon, such as an alcohol or ester CHOH group)
- *83 ppm* (a CH group, confirmed by positive signals
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