Weigh the Mixture Weigh out 5.0 g of the provided mixture into a Erlenmeyer flask. Dissolve in Ether Add 25 mL of tert-butyl methyl ether and swirl until fully dissolved. Use a hot plate if necessary, but do not boil. Prepare for Extraction Check the separatory funnel for tightness. Add the mixture to the separatory funnel and mix gently, venting gas as needed. Separate Layers Allow layers to separate and drain the aqueous layer into a labeled flask. Retain the organic layer. Repeat Extraction Perform two more extractions using the same method as above. Extract with NaOH Extract the organic layer three times with 10 mL portions of aqueous NaOH, draining each time into a separate labeled flask. Combine with Water Add 5 mL distilled water to the organic layer, mix, and drain the water layer into the flask with NaOH extracts. Isolate p-Toluic Acid To the NaHCO₃ extracts, slowly add 6 M HCl until the solution is acidic (pH < 3). Filter using vacuum filtration to isolate the solid. Isolate p-Tert-Butylphenol Heat NaOH extracts to ~60°C. Cool and add 3 M HCl dropwise until acidic (pH < 3). Vacuum filter the crystalline product. Isolate Acetanilide To the organic phase, add 0.75 g anhydrous Na₂SO₄, swirl, and allow to stand. Filter the solution and evaporate the solvent using a rotary evaporator. Induce crystallization by cooling. Melting Point Determination Measure the melting points of crude p-toluic acid, recrystallized p-toluic acid, p-tert-butylphenol, and acetanilide. Record melting ranges. make flow chart for this

1. Weigh the Mixture

   • Weigh out 5.0 g of the provided mixture into a Erlenmeyer flask.

2. Dissolve in Ether

   • Add 25 mL of tert-butyl methyl ether and swirl until fully dissolved. Use a hot plate if necessary, but do not boil.

3. Prepare for Extraction

   • Check the separatory funnel for tightness. Add the mixture to the separatory funnel and mix gently, venting gas as needed.

4. Separate Layers

   • Allow layers to separate and drain the aqueous layer into a labeled flask. Retain the organic layer.

5. Repeat Extraction

   • Perform two more extractions using the same method as above.

6. Extract with NaOH

   • Extract the organic layer three times with 10 mL portions of aqueous NaOH, draining each time into a separate labeled flask.

7. Combine with Water

   • Add 5 mL distilled water to the organic layer, mix, and drain the water layer into the flask with NaOH extracts.

8. Isolate p-Toluic Acid

   • To the NaHCO₃ extracts, slowly add 6 M HCl until the solution is acidic (pH < 3). Filter using vacuum filtration to isolate the solid.

9. Isolate p-Tert-Butylphenol

   • Heat NaOH extracts to ~60°C. Cool and add 3 M HCl dropwise until acidic (pH < 3). Vacuum filter the crystalline product.

10. Isolate Acetanilide

    • To the organic phase, add 0.75 g anhydrous Na₂SO₄, swirl, and allow to stand. Filter the solution and evaporate the solvent using a rotary evaporator. Induce crystallization by cooling.

11. Melting Point Determination

    • Measure the melting points of crude p-toluic acid, recrystallized p-toluic acid, p-tert-butylphenol, and acetanilide. Record melting ranges.

make flow chart for this