Problems Set (Meeting 10)

General Announcements

1. Make sure that you turn in a hardcopy of your research paper by February 13, 2009 at 5 pm and the electronic version to turnitin.com as well (CourseID: 2596847, Passwd: Chem30CL for Winter 2009). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Monday February 16, 2009 at 10 pm, you will receive a "zero" score for the paper. In addition, it will be reported to the Dean of Students. Any plagiarism, partial or full resubmission of a papers or/and other forms of cheating will result in a report to the Dean of Students as well. Make sure that you cite your sources and try to use your own words as much as possible. Here is a checklist what should be included into the report. If you have any questions, please contact your TA or instructor asap, and not an hour before the submission deadline.

2. The next quiz (=quiz 3) will be administered on February 9, 2009 and will cover steps 1 and 2 of the Lidocaine project. Make sure that you show up on time. Otherwise you will not be allowed to take the quiz. No more exceptions!!!!

3. The postlab report for the lidocaine project has to be written in the lab notebook and submitted to the teaching assistant. The due dates are February 17 and February 18, 2009 in your regular lab section.

4. The final product of the lidocaine project has to be turned in to the TA by February 11, 2009 at 5 pm for evaluation by the instructor. Late submission will not receive any credit. Make sure that you label the vial properly.

Questions

1. Referring to the conversion of a-chloro-2,6-dimethylacetanilide to licocaine (step 3), answer the following questions. Show pertinent chemical equations.

a. Why is it important that the a-chloro-2,6-dimethylacetanilide is as dry as possible for this reaction?

b. Toluene is used as solvent in the reaction. Which advantages does this solvent provide?

c. Why does the procedure asks for three equivalents of diethylamine? What does this mean and why is this necessary?

d. During the work-up, the reaction mixture is extracted with 3M hydrochloric acid. Which purpose does this extraction serve? In which layer is the product after the extraction?

e. How is the product recovered after the previous step?

f. How is the crude product dried?