Problems Set (Meeting 9)

General Announcements

1. Formal Report

a. Make sure that you turn in a hardcopy of your research paper by Friday, November 1, 2013 at 4:30 pm and the electronic version to turnitin.com as well (CourseID: 6554023, Password: Chem30CL for Fall 2013 (no spaces!)). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Friday, November 1, 2013 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 report cover (see here) ! Loose paper collections, large binders or folders will not be accepted!!!

2. Quizzes

a. Quiz 4 will be administered on Thursday, October 24, 2013 at 12 pm covering the spectroscopy of epoxides (GC, NMR, MS, IR, etc.). Please make sure that you show up on time, which means at 11:55 am. Otherwise you will not be allowed to take the quiz. Just a reminder, if you do not place your full name and SID on the quiz, you will not receive any credit. Make sure to bring a scientific calculator with you as well.

b. Quiz 5

Quiz 5 will be administered on Thursday, October 31, 2013 at 12 pm. It will cover the entire lidocaine project. Let's hope that it will not be a scary one :-)

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 November 5, 2013 or November 6, 2013 in your regular lab section. The report has to be written in the lab notebook and is worth 15 points.

b. The final product of the lidocaine project has to be turned in to the TA by Wednesday, October 30, 2013 at 5 pm for evaluation by the instructor. Late submission will not receive any credit. Make sure that you label the vial properly. This goes for the GC vial and the sample submitted to the instructor.

4. Grignard Project

a. The Grignard project will start on October 31, 2013.

b.The instructor will provide an in-lab demonstration of the Grignard setup (setup, heating, etc.) on Wednesday, October 30, 2013 at 4:00 pm in YH 6086. Attendance in this demonstration is voluntary (no credit) and is highly advisable for students that feel intimidated by the larger setup. Part of the demonstation will already discussed in lecture prior to this in-lab demo, but certain aspects like heating cannot be shown in the lecture.

5. Research project (Week 9)

a. Please look start looking for a partner for the Ferrocene project. Your partner should be in a different time slot than yourself i.e., if you are in the T/R afternoon section, you will have to find somebody in the W/F afternoon section. This way nobody has to put in additional time outside their regular schedule, which means that each group has four lab meetings to complete the project. We have to avoid as much as possible to have the entire class running around in the lab (Safety!).


Questions (due on 10/24/2013 or 10/25/2013)

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. The anilide has to be very dry. Explain briefly why.

b. The reaction requires three equivalents of diethylamine. Rationalize the choice.

c. Assuming that the student started with 1.5 g of the anilide, which observations should the student make during the course of the reaction? Rationalize this observation.

d. After the reaction was completed, the reaction mixture is first extracted with water and then several times with diluted hydrochloric acid. In which layer is the product afterwards? In which form?

e. How is the product recovered after performing the steps in d.?

f. A student isolates a very small amount of an oily product in the end. How can he acquire an infrared spectrum for his product?

g. The amide proton in lidocaine undergoes a strong intramolecular hydrogen bond. Provide three pieces of evidence for this.