Procedure 1B

Procedure: Project 1 Reaction B

1. Prepare a 70-75°C water bath using the hot plate, a 400 mL beaker, and a clamped thermometer.

2. In a 25 mL round bottom flask, combine a small stir bar, p-methoxyacetophenone (0.15 g) and household bleach (6.0 mL).

2. Attach a reflux condenser and heat the mixture to 70-75°C in the water bath.

3. Monitor the reaction by TLC at ~10-15 minute intervals using 50/50 hexanes/ethyl acetate as the mobile phase. If the reaction is not complete after 30 minutes, add an additional 2.0 mL of bleach and continue monitoring.

4. When the reaction is complete, cool the flask to room temperature.

5. Remove the stir bar and add 10% sodium thiosulfate solution (2 mL) to quench the excess hypochlorite.

6. Swirl the flask to ensure it is well-mixed.

7. Add hydrochloric acid (3M, 2 mL).

8. Collect the resulting solid by vacuum filtration onto a tared filter paper, washing it with distilled water.

9. After drying the solid on the Buchner funnel for at least 45 min, determine the mass of the collected solid.

10. Analyze the product by melting point, IR, and NMR. (Note: The product cannot be analyzed by GC-MS because it is retained by the GC column.)

Reminders & Hints

1. Don’t forget to fully prepare your Lab Notebook according to the guidelines before entering the lab.

2. A variety of resources are available for you to review Thin Layer Chromatography (TLC) under the Lab Techniques section.

3. When you perform your TLCs, you probably want to compare the behavior of the reaction mixture to that of the starting material. You can spot both samples on the same plate. To prepare a standard sample of the starting material, dissolve a rice grain sized amount in ~5 mL acetone.

4. You must complete the Project 1B Prelab Quiz 24h before entering the lab to perform this procedure.

5. Here is a video preview of the reaction, which should help you visualize how to perform this reaction and follow it by TLC in lab: