Three isomers have the molecular formula C,H, OCI. Expanded regions are shown for Isomers 2 and 3. Determine the structure of each isomer and draw in the indicated drawing box. 'H NMR spectrum of Isomer 1 10.0 0'6 6.0 3.0 -to 5.0 4.0 fl (ppm) 8.0 7.0 2.0 1.0 0.0 © University of Michigan L0.002 686'6-

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### Determining the Structure of Isomers of C₇H₅OCl

#### Introduction:
Three isomers have the molecular formula C₇H₅OCl. Expanded regions are shown for Isomers 2 and 3. The objective is to determine the structure of each isomer based on their NMR spectra and draw them in the respective drawing box.

#### ¹H NMR Spectrum of Isomer 1:
Below is the proton nuclear magnetic resonance (¹H NMR) spectrum for Isomer 1. This spectrum, obtained from the University of Michigan, shows the chemical environment of hydrogen atoms within the molecule.

![¹H NMR spectrum of Isomer 1](path/to/spectrum/image)

**Chemical Shifts:**
- A high-intensity peak around 7.262 ppm
- Peaks around 7.469 ppm, 7.509 ppm, 7.630 ppm, 7.888 ppm, and 8.020 ppm 
- Most significant peaks are observed in the aromatic region (6-8 ppm)
- A peak at 9.989 ppm, indicative of a hydrogen possibly attached to an oxygen or highly electronegative group
- An additional peak at 1.00 ppm, which is more upfield

#### Graph Description:
The graph is a typical ¹H NMR spectrum with the x-axis representing the chemical shift in parts per million (ppm) and the y-axis representing the intensity of the signals. The peaks on the graph correspond to different hydrogen environments in the isomer.

#### Deducing Structure of Isomer 1:
Below the spectrum is an interactive drawing tool with options to select, draw, create rings, and erase structures to deduce the structure of Isomer 1. By analyzing the ¹H NMR spectrum presented, one should be able to identify the functional groups and connectivity within the molecule leading to the correct structure of the isomer.

### Interactive Drawing Tool:
- **Select**: Choose preset structures or fragments.
- **Draw**: Freehand draw atoms and bonds.
- **Rings**: Place ring structures easily.
- **More**: Access additional drawing features and tools.
- **Erase**: Correct mistakes by removing atoms, bonds, or fragments.

**Objective**: Using the clues from the ¹H NMR spectrum, deduce the structure of Isomer 1 and draw it in the provided drawing box.

---

For further assistance or
Transcribed Image Text:### Determining the Structure of Isomers of C₇H₅OCl #### Introduction: Three isomers have the molecular formula C₇H₅OCl. Expanded regions are shown for Isomers 2 and 3. The objective is to determine the structure of each isomer based on their NMR spectra and draw them in the respective drawing box. #### ¹H NMR Spectrum of Isomer 1: Below is the proton nuclear magnetic resonance (¹H NMR) spectrum for Isomer 1. This spectrum, obtained from the University of Michigan, shows the chemical environment of hydrogen atoms within the molecule. ![¹H NMR spectrum of Isomer 1](path/to/spectrum/image) **Chemical Shifts:** - A high-intensity peak around 7.262 ppm - Peaks around 7.469 ppm, 7.509 ppm, 7.630 ppm, 7.888 ppm, and 8.020 ppm - Most significant peaks are observed in the aromatic region (6-8 ppm) - A peak at 9.989 ppm, indicative of a hydrogen possibly attached to an oxygen or highly electronegative group - An additional peak at 1.00 ppm, which is more upfield #### Graph Description: The graph is a typical ¹H NMR spectrum with the x-axis representing the chemical shift in parts per million (ppm) and the y-axis representing the intensity of the signals. The peaks on the graph correspond to different hydrogen environments in the isomer. #### Deducing Structure of Isomer 1: Below the spectrum is an interactive drawing tool with options to select, draw, create rings, and erase structures to deduce the structure of Isomer 1. By analyzing the ¹H NMR spectrum presented, one should be able to identify the functional groups and connectivity within the molecule leading to the correct structure of the isomer. ### Interactive Drawing Tool: - **Select**: Choose preset structures or fragments. - **Draw**: Freehand draw atoms and bonds. - **Rings**: Place ring structures easily. - **More**: Access additional drawing features and tools. - **Erase**: Correct mistakes by removing atoms, bonds, or fragments. **Objective**: Using the clues from the ¹H NMR spectrum, deduce the structure of Isomer 1 and draw it in the provided drawing box. --- For further assistance or
**¹H NMR Spectrum of Isomer 2**

The image above displays the proton nuclear magnetic resonance (^1H NMR) spectrum of Isomer 2. This spectrum was provided by the University of Michigan.

### Description of the Spectrum:

- **X-axis (f1, ppm)**: Represents the chemical shift in parts per million (ppm). The chemical shift ranges from approximately 11.0 ppm to -1.0 ppm.
- **Y-axis**: Represents the signal intensity, which indicates the number of protons contributing to each signal.

### Key Peaks and Chemical Shifts:

1. **Peak at ~10.49 ppm**: This is a significant downfield signal, suggesting the presence of a proton in a highly deshielded environment, possibly an aldehyde or carboxylic acid proton.
2. **Cluster of peaks between 8.00 and 7.20 ppm**:
   - A closer analysis (inset box) of the peaks within the range of approximately 8.00 to 7.20 ppm shows various peaks. This region typically represents aromatic protons, indicating the presence of a benzene ring or other aromatic systems.
     - **8.00 ppm to 7.90 ppm**: There are multiple peaks within this region.
     - **7.60 ppm**: Several multiple peaks.
     - **7.50 ppm to 7.40 ppm**: Another set of overlapping peaks.
3. **Peak at ~2.30 ppm to 1.00 ppm**: A smaller, more upfield signal often associated with alkyl groups or protons in a more shielded environment.

### Magnification Inset:
- The inset graph provides a closer look at the peaks between 8.00 ppm and 7.20 ppm. This magnified view helps in distinguishing closely spaced signals, useful for identifying types and environments of protons in aromatic compounds.

**Deduce Structure of Isomer 2:**

Based on the spectrum, one could deduce the structure of Isomer 2 by analyzing the chemical shifts and pattern of the peaks (multiplicity, integration). For instance:

- The downfield peak around 10.49 ppm suggests a conjugation with a strong electron withdrawing group.
- The aromatic region's multi-peak pattern indicates multiple distinct hydrogen environments within the aromatic ring.

### Actionable Steps:
1. Identify and correlate peaks with specific types of hydrogen atoms in the molecular structure
Transcribed Image Text:**¹H NMR Spectrum of Isomer 2** The image above displays the proton nuclear magnetic resonance (^1H NMR) spectrum of Isomer 2. This spectrum was provided by the University of Michigan. ### Description of the Spectrum: - **X-axis (f1, ppm)**: Represents the chemical shift in parts per million (ppm). The chemical shift ranges from approximately 11.0 ppm to -1.0 ppm. - **Y-axis**: Represents the signal intensity, which indicates the number of protons contributing to each signal. ### Key Peaks and Chemical Shifts: 1. **Peak at ~10.49 ppm**: This is a significant downfield signal, suggesting the presence of a proton in a highly deshielded environment, possibly an aldehyde or carboxylic acid proton. 2. **Cluster of peaks between 8.00 and 7.20 ppm**: - A closer analysis (inset box) of the peaks within the range of approximately 8.00 to 7.20 ppm shows various peaks. This region typically represents aromatic protons, indicating the presence of a benzene ring or other aromatic systems. - **8.00 ppm to 7.90 ppm**: There are multiple peaks within this region. - **7.60 ppm**: Several multiple peaks. - **7.50 ppm to 7.40 ppm**: Another set of overlapping peaks. 3. **Peak at ~2.30 ppm to 1.00 ppm**: A smaller, more upfield signal often associated with alkyl groups or protons in a more shielded environment. ### Magnification Inset: - The inset graph provides a closer look at the peaks between 8.00 ppm and 7.20 ppm. This magnified view helps in distinguishing closely spaced signals, useful for identifying types and environments of protons in aromatic compounds. **Deduce Structure of Isomer 2:** Based on the spectrum, one could deduce the structure of Isomer 2 by analyzing the chemical shifts and pattern of the peaks (multiplicity, integration). For instance: - The downfield peak around 10.49 ppm suggests a conjugation with a strong electron withdrawing group. - The aromatic region's multi-peak pattern indicates multiple distinct hydrogen environments within the aromatic ring. ### Actionable Steps: 1. Identify and correlate peaks with specific types of hydrogen atoms in the molecular structure
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