1. General

Review your ¹³C-NMR and DEPT notes.

You need a 50 mL round bottom flask. If you don't have it in your desk, check it out from the lab support. Make sure that the neck size is correct. If you receive a 100ML flask, you will have to insult the flask for better heat retention.


2. Experiment

It is crucial that the cloves soak in cold water prior to the heating process. This will make the eugenol make more accessible for distillation.

The mixture tends to bump into the Hickman head if heated to high and you will have to start over. If you are not sure, place a small beaker with water on the heating block first. A gentle boil indicates that the temperature is not too high. Due to the big amount of solid material, a boiling stones are not working too well.

In order to remove the distillate, you will need a bent the tip of a Pasteur pipette if you don't have a side port (don't forget to place the cap and septum on there!) on your Hickman head. The TA can demonstrate how to do this. More water is added to the flask to keep the liquid volume constant. Otherwise the flask will run dry and no more eugenol will distill over.

A huge excess of drying reagent shoudl be avoided. A small amount is usually sufficent to dry the organic layer.The drying reagent has to be removed prior the evaporation of the solvent.

Do not expect to isolate a huge amount of the final product!



3. Things to think about

a. Why do you use steam distillation to isolate eugenol?

b. Which layer (top or bottom) will contain your product during the extraction,?

c. How can you distinguish between o-, m- and p-xylene using ¹³C{¹H}-NMR spectroscopy?

d. Which are the most pertinent signals in the IR spectrum of eugenol?