Procedure 2

1. In a 25 mL round bottom flask, combine a small stir bar, p-methoxyacetophenone (0.407 g) and glacial acetic acid (3.0 mL).

2. While stirring the mixture on a stir plate, add household bleach (5.5 mL) dropwise.

3. Stir the resulting solution at room temperature for 30 min.

4. Check the progress of the reaction by TLC using 50/50 hexanes/ethyl acetate as the mobile phase. To prepare the TLC sample, remove 1 drop of reaction mixture and dilute it with a few drops of acetone in a test tube. If the reaction is not complete, add an additional 2.0 mL of bleach and check the reaction again after another 20 minutes. Repeat as necessary.

5. After the reaction is complete, add distilled water (15 mL) to the reaction flask. A solid should precipitate.

6. Collect the precipitate by vacuum filtration and wash it with additional distilled water.

7. Recrystallize the solid using 75:25 methanol:water.

7. Dry the crystals on the Buchner funnel for at least 30 min, then determine the mass of the collected solid.

8. Analyze the product by GC-MS: In a vial, dissolve a half-rice-grain sized amount of solid in ~3 mL ethyl acetate. Your instructor will direct you on the use of the instrument.

9. Analyze the product by IR.

10. Analyze the product by NMR: Follow the instructions at the NMR preparations station to prepare an NMR sample in deuterated chloroform (CDCl3).


1. Fully prepare your Lab Notebook according to the guidelines before entering the lab.

2.  To calculate the amount of NaOCl used in the reaction, you may assume that the commercial bleach solution you will use is 6.0% NaOCl by mass. (This means that each 100 mL of solution contains 6.0 g of NaOCl).

3. You must complete the Project 2 Prelab Quiz before entering the lab to perform this procedure.

4. During the TLC analysis, you will want to compare the reaction mixture to the starting material. In a test tube, dissolve a grain of p-methoxyacetophenone in ~1 mL acetone. Use this as your starting material standard and spot it on the same TLC plate as your reaction mixture.