Chemistry - Spring 1999

Course associated with Chemistry 7, introduces students to the most important topics of experimental organic chemistry. The experiments emphasize the applications of organic chemistry to biological systems through the isolation, purification, synthesis and characterization of biologically relevant compounds. In the first weeks the students learn purification and separation techniques such as recrystallization, steam distillation, extraction and chromatography. They then get acquainted with some important aspects of organic reactivity where they apply identification and characterization techniques (IR and polarimetry).
 

The third part of the experimental organic chemistry course. Course associated with Chemistry 112C. Emphasis on organic synthesis and analysis. Students learn HPLC and get extensive practice on IR and NMR. They study of polymers, dyes, proteins, and carbohydrates from an experimental point of view. A challenging class with many applications in the biosciences. The students gain first hand experience in problem-solving in the laboratory.
 

Required Assignments: There will be several written assignments to be done in a professional, complete manner. More details will be made available in class.
Tentative Schedule:
1. Qualitative Organic Analysis: a Two Day Experiment
A number of standard qualitative tests indicative of specific organic functional groups will be carried out on a series of known compounds. In this portion of the experiment, students will work in pairs. Following this, each student will work independently to identify two unknowns following a flowchart utilizing these qualitative tests. The lab report will consist of a record of the results of the qualitative tests on the unknowns, identification of the unknowns, and a clear mechanistic discussion of how each of the 12 qualitative tests work.

Due in class April 13 (one week after completion of the experiment!)
2. Identification of Three Unknowns
Each student will be given a unique mixture of three organic unknowns, which will be separated by standard laboratory procedures. After purification, each of the clean compounds will then be subjected to a variety of spectroscopic analyses (IR, 1H and 13C-NMR, etc.) outlined in class. The student should use this information to successfully identify each of them. The lab report will consist of a record of the separation and purification schemes and yields obtained for each step, the fully assigned and interpreted spectra, and a discussion of the structural analysis.

Due June 4, 1999: Absolutely no reports will be accepted late!
3. Laboratory Notebook
An up-to-date, current laboratory notebook should be kept while doing experiments. The notebook will be checked periodically by the instructor or the T.A., and will be turned in on June 4 with the final assignment.

Grading: Qualitative Analysis 100 pts
Identification of Three Unknowns 300 pts
Technical Skill/Lab Notebook (as evaluated by the instructor and TA) 100 pts
 
note: all assignments must be completed on time to pass the course!

Assignments and Exams: There will be two exams: a midterm worth 100 pts on April 20, and a final exam worth 150 points on April 29. Homework (15 pts per set) will be assigned during the half quarter, and should be turned into Rebecca's mailbox by 10:00 am on Monday the day of the discussion section.
Books on 1-Day Reserve:

The following topics will be covered:
 

Introduction Literature and References Starting Materials Retrosynthetic Analysis Selectivity               Selected Reactions and Processes Cyclizations Baldwin’s Rules Thorpe-Ingold Effect Cationic, Anionic, Radical & Organometallic Cyclizations Other 5-Membered Ring Synthesis Pauson-Khand Carbonyl Condensations Nazarov Cyclization Palladium TMM [3 + 2] Dipolar Cycloadditions

Control of Stereochemistry Relative Diastereoselectivity Ring Systems Acyclic Stereocontrol Felkin-Ahn, Cram Chelation Control Aldol Stereochemistry Allylation of Carbonyls Reconnective Strategy Absolute Stereochemistry Relative Diastereoselectivity using Optically Pure Materials Chirons Classic Resolution Chiral Auxiliaries Enantioselectivity Stoichiometric Asymmetric Induction Kinetic Resolution Catalytic Asymmetric Induction Asymmetric Amplification   Synthetic Strategy Convergence   Atom Economy Strategic Bonds Biomimetic Strategy Key Reaction Strategy Formal Synthesis Computers

 

Revised 7/29/04.