1. General

You should make sure that you are enrolled by now. If not, please see Denise in YH 4009. You will not receive credit for the course, if you are not on the roster when it comes to assigning grades. Due to the fact that you will not be insured if an accident happens in the lab, you will be immediately dismissed from the course.

2. Experiment

Safety note: Diethyl ether is extremely flammable. Avoid any spills on the hot plate. Evaporate the ether off in a warm water bath provided by the TA. Direct evaporation on the hot plate often causes fires! Do not forget to add a boiling stick when you evaporate off the ether to prevent it from bumping. If you cause a fire due to negligance, you will be dismissed from class immediately and receive an "F"-grade.

In the initial stage of the experiment, a setting of 1-2 on the hotplate will provide enough heat for a gentle boil. You do not want to evaporate the entire methanol. Why? Make sure to place a watch glass with ice on the top.

Do not add too much of the drying reagent to the etheral solution. It will make it unnecessarily difficult to separate the liquid and the solid phase later. In addition, you will loose a significant amount of your product as well. Why?

Cap the sodium borohydride bottle after you remove the amount that you need. Why?

Since GC-MS is a very sensitive technique, dissolve only ~2 mg of your dry final product in 1-2 mL of diethyl ether. If you use significantly more, the column will be overloaded and all following samples runs will be difficult. Make sure that you label your vial and write down the bar code number before you give it to your TA.

3. Things to think about

a. How can you distinguish between camphor and isoborneol by IR spectroscopy? Can you distinguish between borneol and isoborneol in the IR spectrum?

b. Assuming that you use racemic camphor, how many products will you isolate? How can you prove this statement?

c. Why do you isolate a mixture of isoborneol and borneol in the reaction?

d. How can you distinguish between borneol and isoborneol?