Problems Set (Meeting 10)

General Announcements

1. Make sure that you turn in a hardcopy of your research paper by November 9, 2006, 2006 at 5 pm and the electronic version to turnitin.com as well (CourseID: 1544420, Passwd: Chem30CL for Fall2006). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Monday November 13, 2006 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 October 30, 2006 at 12 am and will cover step 1 of the Lidocaine project, NMR and GC/MS.

Questions

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

a. Why are three equivalents of diethylamine used in the reaction?

b. After the reaction is completed, the mixture is first extracted with water and then with 3M HCl. Which purpose do these extraction serve? Can they interchanged?

c. Why is the crude lidocaine redissolved in hexane?

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

a. Why is it important to keep the supply bottle of the a-chloroacetyl chloride closed?

b. Why is the use of acyl chlorides often times advantageous compared to the use of carboxylic acids? Give one specific example.

c. The carbonyl stretching frequency of acyl chlorides is generally higher than the one for esters. Rationalize this observation.