Question Completion Status: QUESTION 5 Which of the compounds below would exhibit the FEWEST chemically distinct hydrogens in the ¹H NMR spectrum? CH3 CH3 CH3 CH3 & 6.60 CH3 CH3 с A B D C CA B D CH₂CH3

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Chapter1: Chemical Foundations
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**Question Completion Status:**

**QUESTION 5**

Which of the compounds below would exhibit the FEWEST chemically distinct hydrogens in the \( ^1H \) NMR spectrum?

\[ \text{(A)} \quad \text{Compound with two CH}_3 \text{ groups on a benzene ring in the 1,2-positions (ortho).} \]

\[ \text{(B)} \quad \text{Compound with two CH}_3 \text{ groups on a benzene ring in the 1,3-positions (meta).} \]

\[ \text{(C)} \quad \text{Compound with two CH}_3 \text{ groups on a benzene ring in the 1,4-positions (para).} \]

\[ \text{(D)} \quad \text{Compound with an ethyl (CH}_2\text{CH}_3\text{) group on a benzene ring.} \]

Options:
- B
- D
- C
- A
Transcribed Image Text:**Question Completion Status:** **QUESTION 5** Which of the compounds below would exhibit the FEWEST chemically distinct hydrogens in the \( ^1H \) NMR spectrum? \[ \text{(A)} \quad \text{Compound with two CH}_3 \text{ groups on a benzene ring in the 1,2-positions (ortho).} \] \[ \text{(B)} \quad \text{Compound with two CH}_3 \text{ groups on a benzene ring in the 1,3-positions (meta).} \] \[ \text{(C)} \quad \text{Compound with two CH}_3 \text{ groups on a benzene ring in the 1,4-positions (para).} \] \[ \text{(D)} \quad \text{Compound with an ethyl (CH}_2\text{CH}_3\text{) group on a benzene ring.} \] Options: - B - D - C - A
**NMR Spectrum Analysis and Identification**

The proton NMR spectrum of a compound, \( \text{C}_3\text{H}_6\text{Cl}_2 \), is provided with the following characteristics:
- A pentet at \( \delta 2.19 \)
- A triplet at \( \delta 3.72 \)
- Integration ratio: 1:2

**Objective**: Determine which compound this data corresponds to from the options provided.

**Options**:
A) \( \text{CH}_3\text{CH}_2\text{CHCl}_2 \)
B) \( \text{ClCH}_2\text{CH}_2\text{CH}_2\text{Cl} \)
C) \( \text{CH}_2\text{CHClCH}_2\text{Cl} \)
D) \( \text{CH}_3\text{CH}_2\text{CH}_2\text{Cl} \)

The NMR spectrum shows:

- A tall peak (B) at \( \delta 3.75 \) corresponding to the triplet with relative area 2.00.
- A smaller peak (A) at \( \delta 2.20 \) corresponding to the pentet with relative area 1.00.

The separation between the peaks at \( \delta 3.72 \) and \( \delta 2.19 \) is about 90 Hz, which gives information on coupling constants and the proximity of interacting hydrogens.

**Graph Description**:

- **X-Axis**: Chemical shift in parts per million (ppm) ranging from 0 to 7.
- **Y-Axis**: Relative intensity.
- Peaks are marked with their respective chemical shifts and integration values.
- The graph includes a TMS marker indicating the 0 ppm reference point.

By analyzing the spectrum data and comparing it with possible molecular structures, the best match is **B) \( \text{ClCH}_2\text{CH}_2\text{CH}_2\text{Cl} \)** (1,3-dichloropropane), based on the integration and splitting pattern observed.
Transcribed Image Text:**NMR Spectrum Analysis and Identification** The proton NMR spectrum of a compound, \( \text{C}_3\text{H}_6\text{Cl}_2 \), is provided with the following characteristics: - A pentet at \( \delta 2.19 \) - A triplet at \( \delta 3.72 \) - Integration ratio: 1:2 **Objective**: Determine which compound this data corresponds to from the options provided. **Options**: A) \( \text{CH}_3\text{CH}_2\text{CHCl}_2 \) B) \( \text{ClCH}_2\text{CH}_2\text{CH}_2\text{Cl} \) C) \( \text{CH}_2\text{CHClCH}_2\text{Cl} \) D) \( \text{CH}_3\text{CH}_2\text{CH}_2\text{Cl} \) The NMR spectrum shows: - A tall peak (B) at \( \delta 3.75 \) corresponding to the triplet with relative area 2.00. - A smaller peak (A) at \( \delta 2.20 \) corresponding to the pentet with relative area 1.00. The separation between the peaks at \( \delta 3.72 \) and \( \delta 2.19 \) is about 90 Hz, which gives information on coupling constants and the proximity of interacting hydrogens. **Graph Description**: - **X-Axis**: Chemical shift in parts per million (ppm) ranging from 0 to 7. - **Y-Axis**: Relative intensity. - Peaks are marked with their respective chemical shifts and integration values. - The graph includes a TMS marker indicating the 0 ppm reference point. By analyzing the spectrum data and comparing it with possible molecular structures, the best match is **B) \( \text{ClCH}_2\text{CH}_2\text{CH}_2\text{Cl} \)** (1,3-dichloropropane), based on the integration and splitting pattern observed.
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