Problems Set (Meeting 8)

Announcements (Please read since you will be held to them!)

1. Return of glassware and equipment

a. The lab support usually closes at 5 pm sharp every day. So please make sure to return the glassware clean and on time. Failure to do so will result in a deduction of in-lab points. Note that it is not the instructor's job to provide lab support!

b. Please make sure that you return the equipment that you check out from the instructor i.e., UV-Vis cuvette, polarimetry cells, etc. immediately after your lab section is done. You cannot take the equipment home under any circumstances. Please keep in mind that the equipment is shared with all students in the lab. Failure to observe this rule will result in a significant point penalty.

2. Instrumentation rooms (YH 6076 and YH 6104)

a. The ATR setup has to be cleaned the special wipes that are available from lab support. The wipes should be moistened prior use. It is not acceptable that the student "bathes" the ATR setup in acetone. The acetone will leak into the instrument and ruin any further measurements until it has been "aired out", which takes usually overnight! :-(

b. The area around the FTIR spectrophotometer and the UV-Vis spectrophotometer has to cleaned after usage. This applies to all students and not just the last student. It is unacceptable that samples, Kim wipes, dirty cleaning wipes, boiling sticks, solutions, etc. are left behind. The same goes for the melting point apparatus. The used melting point capillaries have to be disposed off in the glass trash and not left behind or thrown on the floor. The instrumentation room has gotten increasingly filthy over the past two weeks, which is not acceptable due to safety concerns.

3. Experimental

a. You have to finish the first two steps of the lidocaine project on the first day of the project. The anilide has to dry for a significant amount of time in order for the lidocaine synthesis to work properly.

b. The students are required to review the MSDS for all compounds that they are using in the lab. If CAL OSHA inspects the Chem 30CL lab rooms, they might ask the students about this as well. It will make a very bad impression on you as the student, and will speak poorly for the education at UCLA if you do not know even basic information.

4. Quiz 4

1. Referring to the conversion of 2,6-dimethylnitrobenzene to 2,6-dimethylaniline (step 1), answer the following questions. Show pertinent chemical equations where appropriate.

a. Provide a balanced chemical equation for the formation of iron nanoparticles from iron(II) sulfate and sodium borohydride.

b. Where do you see the advantages and the disadvantages of using Fe(np) for the reduction as compared to tin(II) chloride?

c. Why is it important to properly control the temperature during the reduction of the nitro compound? What temperature is the student looking for?

d. Why is solid sodium chloride added to the reaction mixture at the end of the reaction?

e. Which information does the student get from the GC spectrum of the crude?

f. Why is the organic layer of the crude extracted with hydrochloric acid? Which layer contains the product here?

2. Referring to the conversion of 2,6-dimethylaniline to α-chloro-2,6-dimethylacetanilide (step 2), answer the following questions. Show a pertinent chemical equations where appropriate.

a. Assuming the student isolates 1.50 g of 2,6-dimethylaniline in step 1. How many milliliters of the α-chloroacyl chloride should he use in the reaction?

b. Why is it important that the bottle of the acyl chloride is kept close when not in use?

c. What is the function of sodium acetate in the reaction?

d. Why is it important that the acetanilide is dried properly? How is this accomplished?

e. What are the most important changes in the ¹H-NMR spectrum going from 2,6-dimethylaniline to α-chloro-2,6-dimethylacetanilide?