Problems Set (Meeting 10)

General Announcements

Make sure that you turn in a hardcopy of your research paper by Friday May 13, 2005 at 5 pm at YH1217 and the electronic version to turnitin.com as well (CourseID: 1294552, Passwd: Chem30CL for Spring 2005). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Monday May 16, 2005 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.

The next quiz will be on Thursday May 5, 2005 at 11 pm. It will cover the entire Lidocaine project.

Questions

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

a. How many equivalents of diethylamine are used in this reaction? Rationalize.

b. Outline a separation scheme for the isolation of lidocaine.

c. Why is reaction mixture refluxed for 90 minutes?

2. Amides have a relative low stretching frequency for the C=O bond. Explain.

3. How does the ¹H-NMR spectra for N,N-dimethylacetamide differ if acquired at low and at high temperature?

4. Why are acyl chlorides more reactive than esters?