last updated Thursday, May 06, 2010

Problems Set (Meeting 10)

General Announcements

1. Formal Report

Make sure that you turn in a hardcopy of your research paper by Friday, May 7, 2010 at 4:30 pm and the electronic version to turnitin.com as well (CourseID: 3153616, Password: Chem30CL for Spring 2010 (no spaces!)). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Monday, May 10, 2010 at 10 pm, you will receive a "zero" score for the paper. In addition, it will be reported to the Dean of Students for attempted cheating. 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 use your own words. 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. The final version has to be submitted in a small binder! Loose paper collections, large binders or folders will not be accepted!!!

2. Quiz 4

The next quiz will be administered on Thursday, April 29, 2010 at 12 pm. It will cover the entire Lidocaine project. Make sure that you show up on time. Otherwise you will not be allowed to take the quiz. No exceptions!!!!

3. Lidocaine Project

a. 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 May 11, 2010 and May 12, 2010 in your regular lab section. The report is worth 15 points.

b. The final product of the lidocaine project has to be turned in to the TA by Wednesday, May 5, 2010 at 4 pm for evaluation by the instructor. Late submission will not receive any credit. Make sure that you label the vial properly.

4. Grignard Project

a. The project will start on May 6, 2010.

b.The instructor will provide an in-lab demonstration of the Grignard setup on Wednesday, May 5, 2010 at 4 pm in YH 6086.

Questions

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

a. Why is it crucial that the anilide is as dry as possible?

b. Three equivalents of diethylamine are needed for the reaction. Rationalize this choice.

c. Why is it important that the reaction mixture is refluxed here? What does this exactly mean?

d. Many students observe the formation of a white salt during the reaction. Identify the salt and rationalize its formation.

e. At some point during the work-up, the organic layer is extracted with 3 M hydrochloric acid. Which layer is the organic layer at this point? 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 product dried?