Problems Set (Meeting 9)

General Announcements

1. Formal Report

a. Make sure that you turn in a hardcopy of your research paper by Friday, February 7, 2014 at 4:30 pm and the electronic version to turnitin.com as well (CourseID: 7268991, Password: Chem30CL for Winter 2014 (no spaces!)). Late reports will be deducted points (10% per day including the weekend). If you do not submit the report online by Friday, February 7, 2014 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 Tuesday, February 4, 2014 at 9 am covering the spectroscopy of epoxides (GC, NMR, MS, IR, etc.). Please make sure that you show up on time, which means at 8:55 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 will be administered on Tuesday, February 11, 2014 at 9 am. It will cover the entire lidocaine project.

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 February 13 or February 14, 2014 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 Friday, February 7, 2014 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 February 11, 2013.

b.The instructor will provide an in-lab demonstration of the Grignard setup (setup, heating, etc.) on Monday, February 10, 2014 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 we minimize the overcrowding in the lab and a minimum number of students has to put in additional time into the lab outside their regular schedule. Each group has four lab meetings to complete the project. We have to avoid as much as possible to have the entire class 'hanging out' in the lab (Safety!).


Questions (due on 2/4/2014 or 2/5/2014)

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. In lecture it was emphasized several times that the anilide has to be very dry. Explain briefly why and how is this accomplished in the lab?

b. Identify the electrophile and the nucleophile in this reaction.

c. Assuming that the student started with 1.0 g of the anilide, how many milliliters of diethylamine would he have to use in the reaction?

d. After the reaction was completed, a student transfers the reaction mixture into a separatory funnel. He proceeds to extract the mixture with 3 M hydrochloric acid and then with water. What do you think about this?

e. Why is it important that the acidic extract in d. is reacted with a strong base?

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

g. What are the key peaks to be observed in the infrared spectrum of lidocaine?