1. General

Get a lab notebook (you can use the one from Chem 30BL if you still have pages left. This might be a reason to pick up your old lab notebook from Chem 30BL before it is disposed), a lab coat, goggles and nitrile gloves before you come to the lab.The first lab meeting will be on September 25, 2003 at 8 am. If you do not attend your first lab meeting unexcused (being still on vacation is not an excuse because it shows poor planning!), you will lose your spot in the lab.

It might be a good idea to read the lecture material before hand as well since it makes it easier to understand what the instructor is talking about in the lecture. The lecture time allotted for this class does not permit to discuss every aspect in great detail. Aside of that, you are in a higher level class which requires you to do more work on your own as well.

Review: chromatography (LC, TLC, GC), ¹³C-NMR spectroscopy, 2-dimensional NMR techniques, DEPT spectroscopy, extraction theory

You are expected to have a good grasp of these techniques and subjects from Chem 30BL (or Chem 130AL). There is no excuse if you don't know how to apply the knowledge that you acquired previously in general or organic chemistry courses.

2. Literature work

The work sheet can be found here. You will probably not be able to finish the work sheet, but the introduction should be enough to get started on the literature research for your formal report. The draft version for your research paper will be due on October 17, 2003 at 5 pm. This draft version should include the complete introduction and some parts of the project that you have already finished by then including the interpretation of the spectra.

3. Experiment (Formation of the benzylic alcohol, step 2)

a. It is very important that the phenol and sodium hydroxide are completely dissolved. Why?

b. Add the formaldehyde solution slowly. The reaction is exothermic.

c. Make sure that you clamp your flask and place parafilm on the top to seal it off. Place a label with your name, section and TA on the flask.

d. Since the reaction has to run for about 24 hours and there are limited number of hotplates available, the Thursday group has to come back on Friday morning/noon to remove their setup. Place your flask in your drawer. If you are unable to come before 12 pm on Friday (or 8 am on Tuesday), make sure that one of your fellow students removes your flask. If it is still there when the other section enters the lab, the TA will remove it and will dispose of it. As a result you will fall a meeting behind schedule, since you have to repeat the experiment.

e. You will have to start the reaction before you leave the lab to go to the computer lab.

4. Saftety

a. Formaldehyde solution is cancer suspect. Please be careful when handling it. Don't spill it over you and try to avoid breathing the vapors. For more info see http://www.osha.gov/SLTC/formaldehyde/.

b. Sodium hydroxide is a strong base and very corrosive. It damages the skin very fast. It is also very hygroscopic. For more info see http://ptcl.chem.ox.ac.uk/MSDS/SO/sodium_hydroxide.html

5. Things to think about

a. Why does a reaction in nature usually favor one enantiomer over the other one?

b. Which types of chirality are known?

c. Why does often only one enantiomer of a drug work the desired way?

d. Sulfoxides (RR'S=O) are chiral. Why?