Use the information given to explain the following for unknown C3H9CI. 1. Assign the structure for each problem in this set. 2. For each answer provide a commentary that convinces the reader that your structural assignment is correct. You can discuss the evidence for the structure you propose as well as evidence against possible alternatives. 3. Each unique signal in the H NMR spectrum ought to be assigned to the structure.

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**Analysis of Unknown Compound C₈H₉Cl**

**Objective:**
1. Assign the structure for the unknown compound with the formula C₈H₉Cl.
2. Provide evidence supporting the structural assignment using spectral data.
3. Assign each unique signal in the ¹H NMR spectrum to the structure.

**Spectral Data:**

**IR Spectrum:**
- The infrared spectrum displays multiple absorption peaks.
- Broad peak near 3000 cm⁻¹, suggesting C-H stretching (likely aromatic or alkyl groups).
- Peaks around 1600 to 1450 cm⁻¹ may indicate C=C stretching in an aromatic ring.

**¹³C NMR:**
- Chemical shifts are observed at 138.1, 129.0, 128.7, 128.5, 44.8, 39.1 ppm.
- Peaks in the range of 128-138 ppm suggest aromatic carbons.
- Peaks around 40-45 ppm could indicate aliphatic carbons possibly attached to a chlorine atom.

**¹H NMR:**
- The spectrum shows several signals with integrations:
  - Signal at around 7 ppm, integration of 4 (suggesting aromatic hydrogens).
  - Signal at approximately 3-4 ppm, integrations of 2 and 2 (likely aliphatic hydrogens).

**Structural Assignment:**
- Based on the aromatic peaks in both the ¹³C NMR and the integration in the ¹H NMR, the compound likely contains a benzene ring.
- The presence of a chlorine atom suggests that one peak near 40 ppm corresponds to a carbon adjacent to the chlorine.
- Possible structure: Chloromethylbenzene, where a benzene ring is attached to a -CH₂Cl group.

**Conclusion:**
- The combination of IR, ¹³C NMR, and ¹H NMR data supports the structural assignment of the compound as chloromethylbenzene.
- Each signal and integration can be attributed to either aromatic or aliphatic hydrogens in the structure, confirming the analysis.
Transcribed Image Text:**Analysis of Unknown Compound C₈H₉Cl** **Objective:** 1. Assign the structure for the unknown compound with the formula C₈H₉Cl. 2. Provide evidence supporting the structural assignment using spectral data. 3. Assign each unique signal in the ¹H NMR spectrum to the structure. **Spectral Data:** **IR Spectrum:** - The infrared spectrum displays multiple absorption peaks. - Broad peak near 3000 cm⁻¹, suggesting C-H stretching (likely aromatic or alkyl groups). - Peaks around 1600 to 1450 cm⁻¹ may indicate C=C stretching in an aromatic ring. **¹³C NMR:** - Chemical shifts are observed at 138.1, 129.0, 128.7, 128.5, 44.8, 39.1 ppm. - Peaks in the range of 128-138 ppm suggest aromatic carbons. - Peaks around 40-45 ppm could indicate aliphatic carbons possibly attached to a chlorine atom. **¹H NMR:** - The spectrum shows several signals with integrations: - Signal at around 7 ppm, integration of 4 (suggesting aromatic hydrogens). - Signal at approximately 3-4 ppm, integrations of 2 and 2 (likely aliphatic hydrogens). **Structural Assignment:** - Based on the aromatic peaks in both the ¹³C NMR and the integration in the ¹H NMR, the compound likely contains a benzene ring. - The presence of a chlorine atom suggests that one peak near 40 ppm corresponds to a carbon adjacent to the chlorine. - Possible structure: Chloromethylbenzene, where a benzene ring is attached to a -CH₂Cl group. **Conclusion:** - The combination of IR, ¹³C NMR, and ¹H NMR data supports the structural assignment of the compound as chloromethylbenzene. - Each signal and integration can be attributed to either aromatic or aliphatic hydrogens in the structure, confirming the analysis.
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