Chemistry 403 – Advanced Organic Chemistry – Spring 2013
Professor Cheyenne Brindle
Office: Clement 111
Lab: Clement 112
Phone: (860) 297-2479
Email: cheyenne.brindle@trincoll.edu
Required Items:
Text: Classics in Total Synthesis, by K. C. Nicolaou and E. J. Sorenson.
Molecular Modeling Kit
Available in my Office/Library*:
Texts: Advanced Organic Chemistry; Part A: Structure and Mechanism, by F. A.
Carey and R. J. Sundberg*
Organic Structure Analysis, by P. Crews, J. Rodríguez, and M. Jaspars
Modern Physical Organic Chemistry, E. V. Anslyn and D. A. Dougherty*
Optional Upgrade:
Molecular Modeling Kit: HGS Biochemistry Molecular Model Set 5000 BioOrganic Set ($52)
http://www.maruzen.info/hgs/catalog/product_info.php?products_id=31
Course Format: This course will be a mixture of lectures, discussions of total syntheses,
and student presentations. Students will present their own research on different topics
in written, oral, and visual fashion by writing a review article, giving an oral
presentation, and presenting a poster at the Science Symposium from 1-3 pm on Friday,
May 3 in the Oosting Gym.
Academic Honesty: The rules governing academic honesty will be strictly enforced in
both the classroom and in the laboratory. Violations will be reported to the Honor
Council.
Class Attendance: Class participation will be evaluated as part of your grade, thus
attendance is critical. Students who fail to attend class will be asked to drop the course.
Rescheduled Class: Class on February 14 has been rescheduled for Sunday, February
17, 2-3:15 pm.
Problem Sets: During the first part of the course we will have weekly problem sets that
cover the material covered in the lecture component of the course. These problem sets
will generally be due on Friday at the beginning of class. Late assignments will only be
accepted until 5 pm on Friday for a penalty of 2 points. No assignments will be accepted
after that time.
Office Hours: I will typically be in my office or nearby laboratory throughout the day,
except when I am teaching or during the lunch hour. Please feel free to drop by if you
have any questions. My office hours this semester will be Monday and Wednesday 8–10
am, and Thursday 1-3 pm. If you find that these hours present conflicts with your
schedule, please contact me to arrange a more suitable meeting time.
Exam: There will be an open-note exam for this course on April 11 in Clement 215. There
will be no final exam for the course.
Projects: There will be three projects during the course, a 25 minute oral presentation, a
written 5-7 page paper, and a poster. The subject of the first two projects will be a
organic chemistry topic of your choosing, and the poster will be on a total synthesis of
your own choosing from the current literature. I will provide a list of subjects that I find
interesting, but you are welcome to pursue your own topics. You must get approval
from me before you begin your research in order to ensure that the topic is appropriate
for the course and to avoid duplication of topics. These projects will include a revision
process that includes construction of a narrative, outline generation, completing a first
draft and editing.
Grades: Final grades will be determined on the basis of total points accumulated during
the semester. The distribution of points is as follows:
1 hour-long exam
review/presentation
poster
8 problem sets
@ 150 points = 150 points
@ 300 points = 300 points
@ 150 points = 150 points
@ 15 points
= 120 points
Total
= 720 points
Lecture Topics
Synthetic Target
Acidity and pKa’s: a Useful Tool in Predicting Equilibria
Stereochemistry
Advanced NMR Analysis (handout from Organic
Structure Analysis)
Conformation
Retrosynthetic Analysis
menthol (Ch. 22)
amphotericin B (Ch. 24)
Molecular Orbital Theory and it’s Utility for
Understanding Reactivity
periplanone B (Ch. 21),
endiandric acids (Ch. 17)
Enantioselective Synthesis
prostaglandin (Ch. 5)
Asymmetric Epoxidation/Aziridination (Sharpless,
Jacobsen, and Evans)
L-hexoses (Ch.
19)
Asymmetric Reductions (Pfaltz and Noyori, CBS)
menthol (Ch. 22)
Hidden Symmetry
carpanone (Ch. 7)