CHEM 2320 - 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. Chem 2320 has three major chapters:
¥ (a) Core
chapters cover basic synthetic
methodologies and some introductory-level 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 cover selected major
subdisciplines of Organic Chemistry, such as heterocyclic, pericyclic,
medicinal, organometallic, combinatorial, and microwave chemistry.
¥ (c) Advanced chapters will focus on natural product and complex molecule
synthesis strategies, including mid-level retrosynthetic planning. Depending on
the progress the class makes during the first two Chapters, this section might
be shortened.
Every section includes ample examples
from the chemical literature and is concluded by an exam. In all cases, the
rate of progress to the next section depends on class performance as well as
student feedback.
Class
Topics & Partial Lecture Notes: See
our course web page at http://ccc.chem.pitt.edu/wipf/Courses/2320_08.html.
Texts: Carruthers/Coldham
ÒModern Methods of Organic SynthesisÓ (4th Ed.).
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 browsing 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 E769 in
the 2007/8 Sigma-Aldrich labware catalog); optional but highly recommended.
Homework: In addition to selecting problems from textbooks, I
will use the EvansÕ 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. You should also start immediately to brush up on your Name
Reactions. It is a great idea to do the self-assessment quiz and re-read
the sophomore organic textbook.
Journal
Club: Mo
5-6 PM. The
Journal Club presentations are voluntary, but may be used for extra
credit. Please follow the format
of the Sample Presentation. Some material covered in the Journal
Club presentations is likely to appear on Exams. An efficient approach to
quickly identify suitable papers is to check Org. Lett., J. Am. Chem. Soc., Angew. Chem.
Int. Ed., or Methods in
Organic Synthesis (MOS).
Ofc.
Hrs: Tuesdays 5:00-5:50 PM, Room 1301A.
Exams: 2 Midterms; scheduling TBD; 100 points each. In each
exam, 1-2 questions will be dedicated to Name
Reactions; 1-2 questions will also be straight out of a typical sophomore
organic textbook like Vollhardt. Cumulative
Final: Wednesday, April 23, 6:00-8:00 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. Please note that the test will be reconsidered in its entirety. When
you resubmit your test, 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. All lecture materials, 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, quizzes as well as copies of handouts, selected slides and other
course-related information will be posted at http://ccc.chem.pitt.edu/wipf/Courses/2320_08.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 code, please let me know).
Students
with Disabilities: If you have a
disability for which you are requesting an accommodation, 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
accommodations for this course.
Key
to Success: Attend the lectures and
use every opportunity to ask questions and participate in discussions; be
conscientious about homework and literature readings. Discuss the course
materials with your colleagues. Participate in the Journal Club.