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 e.g. AXE (YH1275, http://www.chem.ucla.edu/~AXE/labsupplies.html) before you come to the lab.The first lab meeting will be on March 31, 2009 at 8 am (for those of you who are enrolled or wait-listed in these sections). Attendance during your first meeting is mandatory. If you do not attend during the first 30 minutes, you will automatically lose your spot in the course(being still on vacation is not an excuse because it shows poor planning!). Wait-listed students will be signed up then based on priority (Chem&Biochem majors first, then according to seniority, extension students very unlikely this quarter. Sorry!). Nobody enters the lab before being approved by the instructor!

Required texts are the Course Reader (Organic Chemistry 30CL Reader, Spring 2009), the techniques and spectroscopy reader ("A Short Survival Kit for O=Chem Lab", Spring 2009 (if do not have an earlier version already), the Exam Collection Reader for Chem 30 CL (Spring 2009) and the textbook from J. Mohrig et al. (Techniques in Organic Chemistry). The course reader and the exam collection reader are available as bundle at Course Reader Materials in Westwood (1080 Broxton Avenue, near Rite Aid starting March 30, 2009, open M-F 9-6 pm, S 10-4 pm (first two Saturdays in the quarter only), phone number: (310)443-3303). It is in your best interest to have the latest edition of the readers, since this is the source your TA and the instructor use for lectures, quizzes and exams. This is the wrong place and time to save a few dollars. Look at it as an investment of passing the course.

It is highly advisable to read the lecture material before the lecture since it makes it easier to understand what is covered in the actual 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. The assigned articles for the epoxidation project should be obtained asap (this means on day #1 and not the day before the final paper is due!), because they are very helpful for your in-lab work.

You should also review topics like chromatography (LC, TLC, GC), extraction theory, recrystallization, NMR spectroscopy, 2-dimensional NMR techniques, DEPT spectroscopy, etc before the course starts to get a good start into the practical work. You are expected to have a good grasp of these techniques and subjects from Chem 30BL. There is no excuse if you don't know how to apply the knowledge that you acquired previously in general or organic chemistry courses. If you did not take the courses at UCLA, it is your responsibility to check what was covered in previous courses and if you are really ready to take Chem 30CL at this point in time. However, the instructor will offer additional work-shops on Mondays from (5-6 pm probably starting on March 30, 2009 in tba) to review spectroscopy (IR, NMR, UV-Vis) and other topics of interest (check web site for schedule and topics). The work-shop will start as soon as a room as been assigned (Please check course web site and email for further announcements).


2. In-lab work

a. Literature work (Crossfire)

You will probably not be able to finish the worksheet, 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 April 24, 2009 at 4:30 pm. This draft version should include the complete introduction and some parts of the project that you have already finished by then including the full interpretation of the spectra. Just a hint: Procrastinating will get get you in a lot of trouble in this course since late submission will be deducted a lot of points.

b. Sign-up for Scifinder Scholar

Please register for Scifinder Scholar Web version before April 2, 2009. Instructions are available at: http://software.chem.ucla.edu/scifind

After you have completed the registration process, CAS(Chemical Abstract Service) will send you an email to your "ucla.edu" account.

You will have to follow the instructions in CAS email to complete the registration for Web access.

Questions: Please contact Marion Peters, Chemistry Librarian, mpeters@library.ucla.edu


b. Safety

- Formaldehyde solution is cancer suspect. Please be careful when handling it. Wear gloves when handling the solution. Do not spill it over you and try to avoid breathing the vapors. For more info see http://www.osha.gov/SLTC/formaldehyde/.

- 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

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

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

b. Crushing up the NaOH pellets increases the rate of dissolution. However, this should be done quickly. Why? It is also necessary to seal off the flask at this point to keep the moisture and air out!

c. The phenolate solution should be chilled in an ice-bath before the formaldehyde solution is added slowly.

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

e. Since the reaction has to run for about 24 hours and there are limited number of hotplates available, the sections have to share hotplates.

f. You should start the reaction before you leave for the computer lab. If the sodium hydroxide did not dissolve by then, return after the computer lab to add the formaldehyde then. Afterwards, make sure that you seal off the flask with parafilm!!!!

g. Please make sure to come back the next day to remove the setups from the hot plates, so that the students in the earlier sections have enough room to work as well.

h. It is also highly advisable to use a small Erlenmeyer flask (25 or 50 mL if possible) to minimize the exposure to air.


3. Things to think about

a. What is an ice-bath exactly? Why is it used here?

b. Why is it difficult to dissolve sodium hydroxide in a polar solvent like methanol?

c. Why is imperative to seal off the flask during the reaction?

d. How is the formaldehyde introduced to the reaction?