Problems Set (Meeting 10)

General Announcements

1. Make sure that you turn in a hardcopy of your research paper by Friday, November 6, 2009 at 5 pm and the electronic version to turnitin.com as well (CourseID: 2770701, Password: Chem30CL for Spring 2009 (no spaces!)). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Monday, November 9, 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 4) will be administered on Tuesday, October 27, 2009 at 11 am. It 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 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 November 3, 009 and November 4, 2009 in your regular lab section. The report is worth 15 points.

4. The final product of the lidocaine project has to be turned in to the TA by October 30, 2009 at 5 pm for evaluation by the instructor. Late submission will not receive any credit. Make sure that you label the vial properly.

5. There will be an in-lab demonstration by the instructor on how to set up the Grignard setup on Wednesday, October 28, 2009 at 4 pm and 4:30 pm (if necessary) in YH 6086. Many TAs will provide extra credit for attending this demonstration.

Questions

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

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

b. What is the solvent in this reaction? Rationalize the choice.

c. What should the student observe if the reaction ran according to plan?

d. During the work-up, the reaction mixture is first extracted with water. Which purpose does this extraction serve?

e. Afterwards, the organic layer is extracted with 3 M hydrochloric acid. Which layer contains the product after the extraction? In which form?

f. How is the product recovered after the previous step? How does the product appear at this point?

g. How is the crude product dried?

h. What are the most important peaks in the FTIR spectrum of the product?