Syllabus
Dr. Peter Wipf [pwipf@pitt.edu], 4-8606
CHEMISTRY 2320
12:00-1:15 PM, MW, 228 EBERL
ADVANCED ORGANIC CHEMISTRY 2
This introductory graduate level course presents the basic principles of synthetic
methodology, retrosynthesis, and the tactics and strategies of total synthesis. Chem
2310 is not a prerequisite for this course, however a sound knowledge of the material
covered in the sophomore organic courses 0310 and 0320 (or equivalent) is. There are
three major sections to this course:
• (a) Core chapters on basic synthetic methodologies and retrosynthetic planning.
Asymmetric synthesis is an important characteristic of modern organic chemistry, and
therefore we will often stress enantioselective and diastereoselective processes,
mechanisms, and transition state analysis.
• (b) Special topics, such as heterocyclic, pericyclic, medicinal, organometallic,
combinatorial, and microwave chemistry.
• (c) Advanced chapters on natural product and complex molecule synthesis
strategies.
Every section includes ample examples from the chemical literature and is concluded
by an exam. In principle, progress to the next section depends on class performance.
Class
Topics & Partial Lecture Notes: See our course
http://ccc.chem.pitt.edu/wipf/Courses/2320_07.html.
web
page
at
Journal Club: Mondays 5:00-5:50 PM, 130 CHVRN. Based on student participation;
voluntary, but may be used for extra credit. Please follow the format of
the Sample Presentation. Material covered in the Journal Club is likely to
appear on Exams.
Homework: I will use the Evans’ web site http://evans.harvard.edu/problems/ for weekly
problem assignments. While homework will not be collected or graded
(you are able to access the chemical literature to read up on the
subjects), Exams will make extensive use of analogous questions.
Ofc. Hrs:
Tuesdays 5:00-5:50 PM, Room 1301A.
Texts:
Carruthers/Coldham “Modern Methods of Organic Synthesis”
http://www.cambridge.org/uk/catalogue/catalogue.asp?isbn=0521778301
I will not follow this book closely, but it provides background
supplementary information on most topics that are discussed in the
lectures. All chapters of this book are considered part of the course
material.
Additional references & recommended readings will be given to Advanced
Organic Chemistry, Parts A & B, by F. A. Carey and R. J. Sundberg.
These books are available on-line from the Pitt library:
http://site.ebrary.com/lib/pitt/Doc?id=10046999
http://site.ebrary.com/lib/pitt/Doc?id=10047037
Also recommended for occasional consideration is The Art of Writing
Reasonable Organic Reaction Mechanisms by R. B. Grossman.
http://www.chem.uky.edu/research/grossman/textbook.html
Models:
Darling flexible model kit (Z108006-1KT, $53.20; page E474 in the 2005/6
Aldrich catalog) is optional but highly recommended.
Exams:
2-3 Midterms; scheduling tbd; 100 points each. In each exam, 1-2
questions will be dedicated to Name Reactions.
Cumulative Final: Monday, April 23, 12:00-1:15 PM; 200 points. There
will be no make-up exams. You will have one (1) week from the time your
exams are handed back to submit them for regrade or comments, if you
feel it is necessary (the test will be reconsidered in its entirety). Clearly
mark what should be regraded; it is not allowed to make any changes or
additions on the exam if you intend to submit it for regrading. Cheating in
any form before, during or after an exam will result in an F grade for the
course. Cell phones and PDAs must be turned off and stowed away
during all lectures and exams. For general academic integrity guidelines,
see: http://www.pitt.edu/~provost/ai1.html.
Results for exams and quizzes as well as copies of handouts and slides
and
other
course-related
information
will
be
posted
at
http://ccc.chem.pitt.edu/wipf/Courses/2320_07.html. Please check the
exam scores for accuracy (I will use your student ID number as
identification; if you object to this, or would like me to use another
number, please let me know).
Students with Disabilities: If you have a disability for which you are requesting an
accomodation, please contact me as well as Disability Resources and
Services, 216 WPU (http://www.drs.pitt.edu/), as early as possible in the
term.
DRS will verify your disability and determine reasonable
accomodations for this course.
Key to Success: Attend the lectures and use every opportunity to ask questions; be
conscientious about homework and literature readings. Discuss the
material with your colleagues. Participate in the Journal Club.