NOTE: If the sample of carvone you isolated in Project 3 was relatively pure, you may use it for Project 4. If your carvone sample was impure, or if you did not isolate enough material, use the stock of carvone supplied in the lab.
1. In a 25 mL round bottom flask, add ~0.5 g carvone.
2. Add 5 mL of 6 M HCl and a small stir bar to the flask, attach a reflux condenser, and heat the reaction mixture to a gentle reflux for 1 hour.
3. Remove the reaction flask from the heat and allow the reaction mixture to cool to room temperature.
4. Extract the mixture with ethyl acetate (2 × 10 mL), and then wash the combined organic layers with brine.
5. Dry the combined organic layers with sodium sulfate, gravity filter the mixture, and remove the solvent using rotary evaporation.
6. Determine the mass of your product.
7. Obtain 1H NMR, ¹³C NMR, IR and GC-MS data.
8. Your product can be deposited in the collection bottle provided in the lab.