Problems Set (Meeting 10)

General Announcements

Make sure that you turn in a hardcopy of your research paper by Thursday November 10, 2005 at 5 pm and the electronic version to turnitin.com as well (CourseID: 1313311, Passwd: Chem30CL for Fall 2005). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Monday November 14, 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 administered on Wednesday 9, 2005 at 12 pm.

Questions

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

a. Three equivalents of the amine are used in the reaction. Rationalize this choice.

b. How do you know that the reaction is progressing?

c. The reaction mixture is extracted with water and hydrochloric acid. Explain briefly.

2. Acyl chlorides and ester are more reactive than amides. Rationalize this observation.

3. Why is the ¹H-NMR spectra for N,N-diethylacetamide temperature dependant?

4. A student prepares an epoxide for p-methylstyrene.

a. How many signals would he observe in the ¹H-NMR spectrum? Where are they observed in the spectrum?

b. How many signals would he observe in the ¹³C-NMR spectrum?Where are they observed in the spectrum?