4. Below is an acid-base extraction flow chart. The four compounds seen in the first box was mixed and dissolved in dichloromethane. Complete the flow chart by drawing (bond-line structure) the organic compound that is found in each layer upon each addition. Draw in any relevant charges. OH CN H. 10% HCI ORGANIC AQUEOUS 10% NaHCO3 AQUEOUS ORGANIC 10% КОН AQUEOUS ORGANIC

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**Acid-Base Extraction Flow Chart Explanation**

This flow chart outlines an acid-base extraction process for a mixture of four compounds, dissolved in dichloromethane, to separate them based on their acidic or basic properties.

**Compounds in the Mixture:**
1. Phenol group (OH attached to a benzene ring)
2. Cyanophenyl group (benzene ring with a cyano group, CN, attached)
3. Pyrrole group (NH group in a pyrrole ring)
4. Benzyl alcohol (benzene ring with a CH2OH group attached)

**Extraction Steps:**

1. **Addition of 10% HCl:**
   - The mixture is divided into two layers:
     - **Organic Layer:** Compounds that remain non-reactive in acidic conditions.
     - **Aqueous Layer:** Compounds that are protonated and become water-soluble.

2. **Addition of 10% NaHCO₃ to the Aqueous Layer:**
   - Separates out any phenolic compounds that react with NaHCO₃.
     - **Aqueous Layer:** Water-soluble acidic compounds (phenols).
     - **Organic Layer:** Remaining non-reactive compounds.

3. **Addition of 10% KOH to the Aqueous Layer:**
   - Further separates acidic compounds by converting them into their salts.
     - **Aqueous Layer:** Salt form of acidic compounds.
     - **Organic Layer:** Compounds not reactive to KOH.

**Diagram Explanation:**

The flowchart visually demonstrates the step-by-step extraction process. Each step involves the partitioning of the mixture into organic and aqueous layers, facilitated by the addition of specific reagents (10% HCl, 10% NaHCO₃, 10% KOH). 

Boxes represent the various organic and aqueous layers at each step, where the target compounds are located based on their solubility and reactivity. Each arrow indicates an extraction step, showing how the reagents selectively isolate different components of the original mixture.
Transcribed Image Text:**Acid-Base Extraction Flow Chart Explanation** This flow chart outlines an acid-base extraction process for a mixture of four compounds, dissolved in dichloromethane, to separate them based on their acidic or basic properties. **Compounds in the Mixture:** 1. Phenol group (OH attached to a benzene ring) 2. Cyanophenyl group (benzene ring with a cyano group, CN, attached) 3. Pyrrole group (NH group in a pyrrole ring) 4. Benzyl alcohol (benzene ring with a CH2OH group attached) **Extraction Steps:** 1. **Addition of 10% HCl:** - The mixture is divided into two layers: - **Organic Layer:** Compounds that remain non-reactive in acidic conditions. - **Aqueous Layer:** Compounds that are protonated and become water-soluble. 2. **Addition of 10% NaHCO₃ to the Aqueous Layer:** - Separates out any phenolic compounds that react with NaHCO₃. - **Aqueous Layer:** Water-soluble acidic compounds (phenols). - **Organic Layer:** Remaining non-reactive compounds. 3. **Addition of 10% KOH to the Aqueous Layer:** - Further separates acidic compounds by converting them into their salts. - **Aqueous Layer:** Salt form of acidic compounds. - **Organic Layer:** Compounds not reactive to KOH. **Diagram Explanation:** The flowchart visually demonstrates the step-by-step extraction process. Each step involves the partitioning of the mixture into organic and aqueous layers, facilitated by the addition of specific reagents (10% HCl, 10% NaHCO₃, 10% KOH). Boxes represent the various organic and aqueous layers at each step, where the target compounds are located based on their solubility and reactivity. Each arrow indicates an extraction step, showing how the reagents selectively isolate different components of the original mixture.
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