(1) The three (3) component mixture of fluorenone, ferrocene, and 2-acetyloxybenzoic acid (aka aspirin) shown below was loaded on the column and eluted with 95:5 petroleum ether: diethyl ether. Using the Molecular View of the column provided: (a) draw one (1) molecule of each analyte in the correct relative position in the column, and (b) clearly show the relevant intermolecular forces that explain the column elution order. You do not need to include solvent molecules. (8 points) buret wall AI top of column H Al- AI- H H IIIII -0-H -Ö-H bottom of column -‒‒‒‒‒‒‒. buret wall OH

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### Concept Question

**Question:**
The three (3) component mixture of fluorenone, ferrocene, and 2-acetoxybenzoic acid (also known as aspirin) shown below was loaded on the column and eluted with 95:5 petroleum ether: diethyl ether. Using the **Molecular View of the column** provided: 
(a) Draw one (1) molecule of each analyte in the correct relative position in the column, and 
(b) Clearly show the relevant intermolecular forces that explain the column elution order. You do not need to include solvent molecules. (8 points)

**Diagram Description:**

1. **Simplified Column Diagram**:
    - The top and bottom of the column are indicated.
    - The structure of the column matrix is shown, which consists of recurring units of alumina (Al-OH groups) interacting through hydrogen bonding.

2. **Molecular Structures**:
    - **Fluorenone**: A flat aromatic ketone structure with a carbonyl group (C=O) at its core.
    - **Ferrocene**: A metallocene with an iron (Fe) atom sandwiched between two cyclopentadienyl rings.
    - **2-Acetoxybenzoic acid (Aspirin)**: Consists of a benzene ring substituted with acetoxy (O–CO–CH3) and carboxylic acid (COOH) groups.

**Instructions for Answer (for the student):**

1. **Draw the Molecules**:
    - Place fluorenone, ferrocene, and aspirin at their respective positions within the column diagram.
    - Fluorenone, with its polar carbonyl group, will be positioned where interaction with the alumina via dipole-dipole forces is illustrated.
    - Ferrocene, nonpolar but with possible π-π interactions, will be shown at a higher position in the column due to less interaction.
    - Aspirin, with both hydrogen bonding (from –COOH group) and dipole interactions, would be shown interacting strongly at the mid-to-lower regions of the column.

2. **Intermolecular Forces**:
    - **Fluorenone**: Highlight the dipole-dipole interaction between the carbonyl group (C=O) of fluorenone and the hydroxyl groups (Al-OH) on the alumina.
    - **
Transcribed Image Text:### Concept Question **Question:** The three (3) component mixture of fluorenone, ferrocene, and 2-acetoxybenzoic acid (also known as aspirin) shown below was loaded on the column and eluted with 95:5 petroleum ether: diethyl ether. Using the **Molecular View of the column** provided: (a) Draw one (1) molecule of each analyte in the correct relative position in the column, and (b) Clearly show the relevant intermolecular forces that explain the column elution order. You do not need to include solvent molecules. (8 points) **Diagram Description:** 1. **Simplified Column Diagram**: - The top and bottom of the column are indicated. - The structure of the column matrix is shown, which consists of recurring units of alumina (Al-OH groups) interacting through hydrogen bonding. 2. **Molecular Structures**: - **Fluorenone**: A flat aromatic ketone structure with a carbonyl group (C=O) at its core. - **Ferrocene**: A metallocene with an iron (Fe) atom sandwiched between two cyclopentadienyl rings. - **2-Acetoxybenzoic acid (Aspirin)**: Consists of a benzene ring substituted with acetoxy (O–CO–CH3) and carboxylic acid (COOH) groups. **Instructions for Answer (for the student):** 1. **Draw the Molecules**: - Place fluorenone, ferrocene, and aspirin at their respective positions within the column diagram. - Fluorenone, with its polar carbonyl group, will be positioned where interaction with the alumina via dipole-dipole forces is illustrated. - Ferrocene, nonpolar but with possible π-π interactions, will be shown at a higher position in the column due to less interaction. - Aspirin, with both hydrogen bonding (from –COOH group) and dipole interactions, would be shown interacting strongly at the mid-to-lower regions of the column. 2. **Intermolecular Forces**: - **Fluorenone**: Highlight the dipole-dipole interaction between the carbonyl group (C=O) of fluorenone and the hydroxyl groups (Al-OH) on the alumina. - **
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