Problems Set (Meeting 10)

General Announcements

1. Make sure that you turn in a hardcopy of your research paper by May 11, 2007 at 5 pm and the electronic version to turnitin.com as well (CourseID: 1822529, Passwd: Chem30 CL for Spring 2007). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Monday May 14, 2007 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 will be administered on May 9, 2007 at 12 pm and will cover step 3 of the Lidocaine project, NMR and GC-MS of epoxides.

3. The postlab report for the lidocaine project has to be written in the lab notebook and submitted to the teaching assistant.

4. The final product has to be turned in to the TA by May 11, 2007 at 5 pm for evaluation by the instructor. Late submission will not receive any credit.

Questions

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

a. Why is toluene used as solvent in this reaction?

b. Why is an excess of diethylamine used in this reaction?

c. Why is it imperative that the anilide is as dry as possible before proceeding with this step?

d. Outline a separation scheme for lidocaine starting after the reaction was terminated. Indicate clearly what the organic/aqueous layer is, and which product is in which layer.

e. How is lidocaine dried in this reaction?