Spring 2005 Advance Course Information

This information effective for Spring 2005. Check with instructor the first day of class for any changes.

Chemistry

[CHEM-146A] [CHEM-240F]

146A. Advanced Laboratory in Organic Chemistry

TTh 1:00-5:00 p.m., Thimann 249
Instructor: Rebecca Braslau (braslau@chemistry.ucsc.edu)
Office: Thimann 337, tel. 459-3087
Office Hours: 1:30-3:30 Wednesday

Teaching Assistant: Anna Tsimezon
Office: Thimann 331, tel. 459-4525
E-mail: annat@chemistry.ucsc.edu

Course Description:

Prerequisite: successful completion of the Chemistry 108 (A, B, L, and M) series or Chemistry 112 (A, B, C, L, M, and N) series or consent of instructor

Required Assignments: There will be two written assignments to be done in a professional, complete manner. More details will be made available in class. There are two distinct laboratory experiments to be completed.

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 12, 2005 (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. First draft is due Thursday, May 26, although you are encouraged to turn it in earlier! Please have your report corrected for spelling and grammar (by someone else!) before you turn in your first draft.

Final Draft Due Thursday, June 2, 2005, before 12:00 noon (in Rebecca's office). 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 9 with the final assignment.

Note: all assignments must be completed on time to pass the course!
No Make-up laboratory sessions will be arranged!

Absences: If you absolutely need to miss a lab, pre-arrange your absence with the instructor. The two-day qualitative analysis experiment cannot be postponed; however, there is some flexibility in the unknown identification experiment. This does not mean that you are free to miss labs on a causal basis. Non-prearranged absences can be grounds for a No Pass or Fail in this class.

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240F. Selectivity and Strategy in Organic Synthesis

First 5 Weeks of Spring Quarter 2005

TTh 10:00 -11:45 a.m., plus Friday April 29
Social Sciences II Rm 137
Instructor: Rebecca Braslau
E-mail: braslau@chemistry.ucsc.edu
Office: Thimann 337
Phone: 459-3087, office hours Wed. 1:30-3:30 or by appt.
Discussion Section: Wed nights, 7:00 p.m., Thimann 339 on April 13, 20, 27

Course Description

This is a 5-week course designed to follow Chemistry 240E, Modern Synthetic Reactions, offered by Professor Singaram. Prerequisite: Chemistry 240E or consent of instructor

Assignments and Exams: There will be two exams: a midterm worth 100 pts on April 21 and a final exam worth 150 points on Friday, April 29. Three sets of homework (15 pts per set) will be assigned during the half quarter and should be turned into Rebecca's mailbox by 10:00 a.m. on Wednesday, the day of the discussion section. Attendance at the discussion sections on Wednesday nights is mandatory.

No single text will be used, although the following reference books are available in the library:

• March, Advanced Organic Chemistry
• Noyori, Asymmetric Catalysis in Organic Synthesis
• Ager, Asymmetric Synthetic Methodology
• Mulzer, Organic Synthetic Highlights
• Fuhrhop & Penzlin, Organic Synthesis: Concepts, Methods, and Starting Materials
• Seyden-Penne, Chiral auxiliaries and ligands in asymmetric synthesis
• Morrison, Asymmetric synthesis, Vol. 4 (contains a list of optically active starting materials)
• Carruthers & Coldham, Modern Methods of Organic Synthesis

The following topics will be covered:

Introduction

Literature and References
Starting Materials
Retrosynthetic Analysis
Selectivity

Selected Reactions and Processes

Cyclizations: general concepts

Baldwin's Rules
Thorpe-Ingold Effect

Types of Cyclizations

Cationic

Nazarov, etc.

Anionic
Radical
Organometallic Cyclizations

Palladium TMM
Heck
Ring Closing Metathesis

Pauson-Khand

Dipolar [3 + 2] 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

Synthetic Strategy

Convergence
Atom Economy
Strategic Bonds
Biomimetic Strategy
Key Reaction Strategy
Formal Synthesis
Computers

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