CHEM 329: ADVANCED ORGANIC CHEMISTRY LABORATORY
SPRING 2009

TH 2:00-4:50 pm PL 310, PL 202

This course is required for chemistry majors

Design of organic synthesis, including analysis of current literature, practical laboratory experience, identification, purification of organic compounds, and presentation of research results

Summary of the course
1. Each team of two students will receive an unknown organic compound and identify it, using instrumental analysis, physical and chemical tests of the students' choice.
2. The team of students turns in a short written report, supporting the elucidated structure.
3. The instructor assigns to each team a compound that should be synthesized from the identified compound in several steps.
4. The team searches original chemistry literature for the appropriate synthetic procedures to solve the synthetic challenge from the part 3.
5. The team presents the proof of identity of the unknown compound and the found synthetic approach to the class, develops a detailed experimental plan, and turns it in for the instructor's approval.
6. The team advances toward synthesis of the target compound by the procedures selected in part 5, characterizes the final and all intermediate products, turns in the laboratory report and the synthesized compound to the instructor.
7. During the semester, each student learns all experimental techniques employed in the course including the ones not related to his (her) synthetic project.
8. Each student turns in the written final experimental report (synthetic project results plus learned procedures) to the instructor and presents it to the class.

Note: All compounds synthesized during this laboratory course, will be further used for research. No products will go to the waste.

This course is managed through d2L. If you have any technical questions regarding this software, direct your questions to your instructor or to the USD IT Helpdesk.

NOTE: If you have a disability for which you are or may be requesting an accommodation, you are encouraged to contact both your instructor and Dr. Elaine Pearson, Director of Disability Services (Service Center 119, 677-6389) as early as possible in the semester.

MATERIALS REQUIRED:
1. The Organic Chemistry Laboratory Survival Manual, 5th or later Edition (J.W.Zubrick)
2. Safety Glasses or Goggles: Must provide adequate front and side protection.
3. Laboratory Notebook: bound notebook; ca. 8" X 10". Spiral and loose-leaf notebooks are not acceptable.

LABORATORY SAFETY POLICIES: Failure to follow laboratory safety practices could result in your immediate dismissal from the laboratory, without credit for that experiment.

1. EYE PROTECTION MUST BE WORN AT ALL TIMES
2. Pregnant students are advised not to work in organic laboratories. If you are, suspect to be, or become pregnant, notify the instructor immediately.
3. Eating, drinking, chewing gum, etc, are prohibited in the laboratory.
4. Avoid getting chemicals on your skin. If you happen to do so, wash the affected area immediately. Avoid rubbing your eyes, etc. while in the laboratory. Wash your hands thorougly immediately after leaving the laboratory.
5. Know the location of all safety equipment and fire escapes.
6. Use the fume hood when directed to do so.
7. Do not performed unauthorized experiments or alter the designated procedure without obtaining permission.
8. Dress for the laboratory - Clothing worn in the laboratory should provide maximum protection. Open toed/heeled shoes, sandals, etc., and high heels/platforms are not permitted. Long hair must be tied or pinned back. Do not wear your favorite or (and) very expensive items, as they may be destroyed or permanently stained by some chemicals.
9. When lighting a burner, make sure there are no flammable solvents in the area.
10. Even though you are working carefully, don't assume you or someone else won't have an accident that could injure you.
11. Keep your laboratory bench and common areas (balances, hoods, etc.) clean and free of clutter at all times.
12. Report all accidents (cuts, burns, other injuries, spills, fires, explosions, etc.) to the instructor immediately.

You are financially responsible for the equipment loaned to you for this course - that is, you will have to pay for missing or damaged equipment

All students must check out of the laboratory by the last scheduled laboratory meeting. Students failing to do so will recive a grade of "Incomplete".

You are required to keep a laboratory notebook documenting all of your work in this laboratory. Lab notebooks will be checked regularly.

BOR and USD requirments:
1. Freedom in learning.  Students are responsible for learning the content of any course of study in which they are enrolled. Under Board of Regents and University policy, student academic performance shall be evaluated solely on an academic basis and students should be free to take reasoned exception to the data or views offered in any course of study. Students who believe that an academic evaluation is unrelated to academic standards but is related instead to judgment of their personal opinion or conduct should contact the dean of the college which offers the class to initiate a review of the evaluation.

2. If you have a disability for which you are or may be requesting an accommodation, you are encouraged to contact both your instructor and the Director of the Office of Disability Services, (Service Center 199; 677-6389) as early as possible in the semester.

3. No credit can be given for a dishonest assignment. At the discretion of the instructor, a student caught engaging in any form of academic dishonesty may be:
a. Given a zero for that assignment.
b. Allowed to rewrite and resubmit the assignment for credit.
c. Assigned a reduced grade for the course.
d. Dropped from the course.
e. Failed in the course.

Students who missed two or more laboratory periods without an excusable reason, may be dropped from the course by the instructor.

Grading: Your grade will be determined as follows: The total number of points, as listed below, will be calculated.

Identification report 10 points
Spectroscopy quiz 30 points
Identification and synthetic design presentation (peer reviewed) 30 points
Laboratory notebook 10 points
Individual report 20 points
Teammate evaluation 20 points
Final presentation (peer reviewed) 30 points
TOTAL 150 points

Letter grades will then be assigned on the basis of the percentage of points accumulated, with cutoffs no higher than listed below.

A– 90% percentile
B – 80% percentile
C – 65% percentile
D– 50%

Identification report (team prepared) is a written 1-2 pages explanation how the unknown compound wes explored, and how the experimental data support the suggested structure.

Specrtoscopy quiz Ten written response questions, testing your understanding of NMR-, IR-, and mass-spectroscopy

Identification and synthetic design presentation (team prepared)is an oral presentation of the identification and the literature search results, evaluated by your classmates and the instructor, according to the following criteria:
1. Knowledge of NMR (3 points), IR (3 points), Mass-spectroscopy (2 points).
2. Ability to apply the instrumental analysis and chemical tests to elucidate the structure (2 points).
3. Quality of the literature search (5 points)
4. Understanding of chemical reactions behind the found procedures (5 points)
5. Critical analysis of the found procedures (5 points)
6. Quality of the presentation (5 points)

Laboratory notebook will be graded, according to the same criteria as for the CHEM 326L/CHEM 328L courses.

Individual report is a writen description of the performed experiments, according to the Journal of Organic Chemistry style (Experimental section).

Teammate evaluation is an evaluation of your personal contribution to the team project by your teammate, according to the folowing crteria:
1. Your contribution to the literature search (4 points)
2. Your contribution to the team presentations (4 points)
3. Your contribution to the performing of experiments (4 points)
4. Your contribution to the cleaning up the laboratory bench (4 points)
5. Your contribution to the design of experiments (4 points)

Final presentation is an oral presentation of the student's contribution to the team project results and the experimental techniques, learned in the laboratory. The presentation is evaluated by your classmates and the instructor, according to the folowing crteria:
1. Synthesis and purification of compounds (10 points)
2. Characterization of the intermediate and the final products (10 points)
3. Knowledge of the experimental procedures, not relevant to the team project (5 points)
4. Individual contribution to the team project (consistency with the teammate's presentation) (5 points)

SCHEDULE OF CLASS SESSIONS

Date Room Activities
Jan 15   No laboratory. The first week of classes.
Jan 22 PL 310 Introduction. Safety instruction. Spectroscopy lecture.
Jan 29 PL 202 Identification of unknowns
Feb 5 PL 310 Spectroscopy quiz. Assignment of synthetic projects. Lecture on SciFinder. Identification reports due.
Feb 12 PL 310 Identification and Synthetic design presentations
Feb 19, 26, Mar 5, 19, 26, Apr 2, 9, 16 PL 202 Synthesis of target compounds
Apr 23 PL 310 Final presentations. Laboratory notebooks due, Individual reports due. Teammate evaluation due.
Apr 30 PL 202 Student evaluation. Cleaning up (I mean it). Check out.

IF YOU HAVE QUESTIONS, ASK THEM. If you can not stop by you instructor's office during the office hours, make an appointment or just walk-in.