Let's analyze the flowchart step by step: --- ## Step 1: Mixture in Ether Solution - The mixture contains **benzoic acid**, **ethyl 4-aminobenzoate**, and **9-fluorenone** in ether. --- ## Step 2: Add 3 M NaOH - **Benzoic acid** (acidic) reacts with NaOH to form its **sodium salt**, which is **water-soluble** and thus moves to the **aqueous layer (B)**. - **Ethyl 4-aminobenzoate** (an ester with an amine group, but the amine is not basic enough to react here) and **9-fluorenone** (neutral ketone) remain in the **ether layer (A)**. --- ### After NaOH Addition: - **A (Ether Layer):** Contains **ethyl 4-aminobenzoate** and **9-fluorenone**. - **B (Aqueous Layer):** Contains **benzoic acid salt** (sodium benzoate). --- ## Step 3: Add 3 M HCl to B - **B**: Adding HCl to sodium benzoate **re-precipitates benzoic acid** (since it becomes insoluble in water). - The precipitated benzoic acid can be separated (likely in E), while the aqueous layer is separated. --- ## Step 4: Add 6 M HCl to A - **A**: Adding strong acid (HCl) will **not affect ethyl 4-aminobenzoate** (as the amine is not basic enough to react in ether) and **9-fluorenone** (neutral) remains. - Likely, this step is to check if anything moves to aqueous (amine salt formation at very high acid concentration), but here, both likely stay in ether. --- ## Step 5: Add 6 M NaOH to E - **E**: After precipitating benzoic acid, if any remains, adding NaOH would dissolve it as sodium benzoate. --- ## Step 6: Understand Each Statement ### Statement Analysis: 1. **A will contain a solution of ethyl 4-aminobenzoate and 9-fluorenone.** - **TRUE**. Both are neutral/weakly basic and stay in ether after NaOH extraction. 2. **F will contain dissolved 9-fluorenone.** - **FALSE**. F is from E (aqueous benzoic acid salt), so it will not contain 9-fluorenone. 3. **E will contain dissolved benzoic acid salt.** - **TRUE**. E is the aqueous layer after HCl addition to B, so it contains sodium benzoate (benzoic acid salt). 4. **D will contain dissolved 9-fluorenone.** - **TRUE**. D is from the ether layer after HCl addition to A, which still contains 9-fluorenone. 5. **A will contain a solution of benzoic acid and 9-fluorenone.** - **FALSE**. Benzoic acid is extracted into aqueous layer (B) after NaOH addition. --- ## **Final Answers:** - [x] **A will contain a solution of ethyl 4-aminobenzoate and 9-fluorenone.** - [ ] F will contain dissolved 9-fluorenone. - [x] **E will contain dissolved benzoic acid salt.** - [x] **D will contain dissolved 9-fluorenone.** - [ ] A will contain a solution of benzoic acid and 9-fluorenone. --- ### **Summary Table** | Statement | True/False | Reasoning | |-----------|:----------:|-----------| | A will contain a solution of ethyl 4-aminobenzoate and 9-fluorenone. | ✅ | Both are neutral/weakly basic, stay in ether. | | F will contain dissolved 9-fluorenone. | ❌ | F is from aqueous phase after benzoic acid salt. | | E will contain dissolved benzoic acid salt. | ✅ | E is the aqueous layer after precipitating benzoic acid. | | D will contain dissolved 9-fluorenone. | ✅ | D is from ether layer after HCl addition, still contains 9-fluorenone. | | A will contain a solution of benzoic acid and 9-fluorenone. | ❌ | Benzoic acid is extracted as salt into aqueous layer. |