Advanced
Organic Chemistry: Synthesis (CHEM 311/511)
Fall 2007
Prof. W. P. Malachowski
Office: 270 Park
Phone: Ext. 5016
e-mail: wmalacho@brynmawr.edu
web page: http://www.brynmawr.edu/chemistry/malachowski
course web page: http://www.brynmawr.edu/chemistry/malachowski/AdvOChem/AdvOChem.html
Class meetings:
Tues. and Thurs. 11:40-1:00 PM. All class
meetings will be held in PSB 278.
Office Hours: Wed. 9:30-11:00 AM, Tues. 4:30-5:30 PM and by appointment
Textbook: March’s Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 6th edition (2007) by Michael B. Smith and Jerry March
Additional References
Books in Stacks:
-Advanced Organic Chemistry: Reactions,
Mechanisms and Structure, 4th edition (1992) by Jerry March; 5th
edition (2001) by Michael B. Smith and Jerry March
-Advanced Organic Chemistry, Part A:
Structure and Mechanisms, 4th edition (2001) by Francis A. Carey and
Richard J. Sundberg
-Advanced Organic Chemistry, Part B:
Reactions and Synthesis, 4th edition (2001) by Francis A. Carey and
Richard J. Sundberg
-Advanced Organic Chemistry: Reactions and
Mechanisms, (1998) by B. Miller
-The Logic of Chemical Synthesis,(1989) by
E. J. Corey and X.-M. Cheng
-Protective Groups in Organic Synthesis, 3rd
edition (1999) by Theodora W. Greene and Peter G. M. Wuts
-Organic Reactions, Wiley (1942-2007)
-Organic Synthesis, 2nd edition (2001) by Michael B. Smith
Books in Reference Section:
-Comprehensive Organic Synthesis:
Selectivity, Strategy, and Efficiency in Modern
Organic Chemistry, (1991) eds. Barry M. Trost
and Ian Fleming
-Comprehensive Organic Transformations: A
Guide to Functional Group Preparations, 2nd edition (1999) by Richard C. Larock
-Comprehensive Organometallic
Chemistry, (1982) eds. G. Wilkinson, F. G. A. Stone, E. W. Abel
-Comprehensive Organometallic
Chemistry II, (1995) eds. G. Wilkinson, F. G. A. Stone, E. W. Abel
-Encyclopedia of Reagents for Organic
Synthesis, (1995) Leo Paquette
-Handbook of Reagents for Organic Synthesis (1999)
Good Review Article in the Literature:
-"The Art and Science of Total Synthesis
at the Dawn of the Twenty-First Century", K. C. Nicolaou,
D. Vourloumis,
Class Schedule:
|
Week |
Tuesday |
Thursday |
Lecture Topic (Text |
|
1 |
9/4 |
9/6 |
Introduction and Enolate Chemistry (pp. 167-172, 356-366, 375-394) |
|
2 |
9/ 11 |
9/13 PS #1 |
Enolate and Aldol Reactions (sects. 10-67 to 10-70; 10-72; 16-34 to 16-38) |
|
3 |
9/18 |
9/20 |
Conjugate Addition Reactions (sects. 15-24 to 15-28; 15-31) |
|
4 |
9/25 PS #2 |
9/27 |
Alkene Synthesis (sects. 16-44, 18-37) and Protecting Groups |
|
5 |
10/2 |
10/4 PS #3 |
Oxidation Reactions (pp. 1703-1786) |
|
6 |
10/9 |
10/11 |
Oxidation Reactions (cont.) |
|
Fall Break |
10/13-10/21 |
|
|
|
7 |
10/23 |
10/25 PS #4 |
Reduction Reactions (pp. 1786-1869) and Hydroboration (pp. 1075-1082) |
|
8 |
10/30 |
11/1 |
Organometallic Chemistry (sects. 10-57, 12-22, 13-17) |
|
9 |
11/6 PS #5 |
11/8 |
Organopalladium Chemistry (sects. 13-9, 13-10, 13-12, 13-13) |
|
10 |
11/13 |
11/15 PS #6 |
Diels-Alder Reaction (sects. 15-60 and 15-61) and 1,3-Dipolar Cycloaddition (sect. 15-58) |
|
11 |
11/20 |
Thanksgiving Break |
Open |
|
12 |
11/27 |
11/29 Exam 2 |
Sigmatropic Rearrangements (sects. 18-32 and 18-33) |
|
13 |
12/4 |
12/6 |
Open |
|
14 |
12/11 |
12/13 |
Student Oral Presentations |
Problem Sets:There will be six take-home problem sets which will be collected at the beginning of class on the date shown on the schedule above. You may work in study groups to complete the problem sets, but you should submit your own version of the problem set solution.
Exams: There will be two mid-semester exams given during the class meeting time on October 11 and November 29.
Oral Presentation: Students will work in groups of two or three to present a recent article from the organic chemistry literature to the class. The literature article will be chosen by the students from a selection of articles on organic chemistry topics assembled by the instructor. Student groups will have 30-45 minutes to deliver a presentation which explains the context and significance of the literature article while exploring the experimental details of the research.
Final Exam: There will be a three-hour self-scheduled final exam
without lecture notes, textbook or any other associated course materials.
Course Grading:
|
Problem Sets |
20 pts. (x6) |
=120 pts. |
|
Mid-term Exams |
100 pts. (x 2) |
=200 pts. |
|
Oral Presentation |
|
=100 pts. |
|
Self-scheduled Final Exam |
|
=150 pts |
|
|
|
_________ |
|
570 pts. |
Approximate Grading Scheme:
|
95-100% |
4.0 |
73-76% |
2.0 |
|
90-94% |
3.7 |
70-72% |
1.7 |
|
87-89% |
3.3 |
67-69% |
1.3 |
|
83-86% |
3.0 |
63-66% |
1.0 |
|
80-82% |
2.7 |
<63% |
0.0 |
|
77-79% |
2.3 |
|
|
I reserve the right to make modifications to this scheme when I consider it necessary.
Students with Disabilities: Any student eligible for and needing academic adjustments or accommodations because of a disability is requested to speak with me within the first two weeks of class.