Problems Set (Meeting 10)

General Announcements

1. Make sure that you turn in a hardcopy of your research paper by February 16, 2007 at 5 pm and the electronic version to turnitin.com as well (CourseID: 1731193, Passwd: Chem30CL for Winter 2007). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Monday February 19, 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 February 8, 2007 at 12 am and will cover step 1 and step 2 of the Lidocaine project.

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 February 16, 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. How does the experimenter know that the reaction is progressing?

b. After the reaction is completed, the mixture is first extracted with water. Which purpose do this extraction serve?

c. Why is the crude lidocaine redissolved in hexane?

d. What are the major changes going from 2,6-xylidine to lidocaine in the IR spectrum?

2. Acyl chlorides are often used in synthetic organic chemistry. Show pertinent chemical equations.

a. The procedure asks to keep the supply bottle for the acid chloride closed if not used. Explain briefly why.

b. Suggest two methods to obtain acyl chlorides from their corresponding carboxylic acids.

c. Acyl chlorides are often used to obtain esters for tert. alcohols. Explain why and how is this accomplished?