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Chemistry 647 Syllabus
Advanced Organic Chemistry-Synthesis
Chem 647
Spring 2011
Instructor: Jeff Davis
Office: Chemistry 3345 Phone: 5-1845
Electronic: jdavis@umail.umd.edu
Lecture Time & Location: TR 9:30-10:45 in Chemistry 1228
Office Hours: By appointment, designed to fit your schedule-take advantage
Description: This is a 4th semester course in organic chemistry. This will not be a typical lecture course.
Class time will be spent on student-led problem solving, discussion and presentations. We will use
selected problems, the primary literature and the Anslyn and Dougherty text to guide us. Topics will
include conformation, mechanism, reactive intermediates and synthesis.
Objectives: a) To learn how to study and apply the principles of organic chemistry to synthesis and to
your own interests. b) To learn how to organize, understand and present complex information.
c) To improve your reading and writing and presentation skills.
Background: The course is intended for first-year graduate students and advanced undergraduates.
Students should be familiar with the fundamentals of organic chemistry: nomenclature, structure and
bonding, reaction mechanisms and stereochemistry.
Recommended Reference Text: Modern Physical Organic Chemistry Anslyn and Dougherty
The text will be supplemented with articles from the literature and with numerous problem sets.
Just a few Web Resources:
A great site for organic mechanism problems
http://evans.harvard.edu/problems/index.cgi
For a nice link to Comprehensive Organic Chemistry
http://www.chem.wisc.edu/areas/organic/index-chem.htm
Bordwell’s pKa Tables
http://www.chem.wisc.edu/areas/reich/pkatable/index.htm
Hans Reich “Advanced Organic Chemistry”
http://www.chem.wisc.edu/areas/reich/chem547/index.htm
Tentative Schedule
During the course of the semester we'll try to cover some the following topics using problems and the
current literature. Some material may be review for you, some may material may be new to you:
Conformation
Nucleophilic Substitutions
Nucleophilic Acyl Substitutions
Eliminations
Electrophilic Additions
Oxidation/Reduction
“Name Reactions”
Nucleophilic Additions
Rearrangements
Enolates
Organoboron
Organosulfur
Nucleophilic Metal Reagents
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Chemistry 647 Syllabus
Outline of Assignments
Class Schedule: We will work problems on Tuesdays. On Thursdays we will discuss literature articles.
One person will lead discussion in each class period. The person listed for the Thursday class will be
responsible for presenting a 20-minute overview of that day’s assigned paper, either a powerpoint
presentation, a chalk talk or both. A detailed schedule is attached to this syllabus.
Homework: Problems will be assigned on Thursdays and discussed in class on Tuesday. Class
participation counts, so please come prepared to answer and to ask questions. Papers from the literature
will be assigned on Tuesdays and we will discuss those papers on the following Thursday. Again, please
read and study the papers so that you can participate in the analysis of the paper.
Exams: There will be 1 take-home exam and a take-home final. Below, are the exam deadlines. You
have a few days to work on the questions. I have 2 requirements: 1) you work alone on these take-home
exams and 2) written answers are typed. Structures can be hand-drawn, but they must be legible.
Exam Dates: Mid Term Exam - Hand out March 15
Final Exam-Hand out Tues May 10
Due on Friday March 18
Due on Thursday May 12
ChemTract Papers: There will be 2 papers due during the semester. The papers will be written in
ChemTracts format, analyzing a topical article. Before passing the papers in to me, these papers will be
reviewed and evaluated by your peers. Final “teams” and rules will be decided as we progress.
Independent Proposal: The guidelines for the independent proposal will be provided later.
The goal is to write a research proposal involving some organic synthesis that might be “doable” in a
2-year period. You may choose 1 of the following organic chemistry labs to focus on:
David MacMillan
Micahel Krische
Erick Carreira
Carlos Barbas
Laura Kiessling
Carolyn Bertozzi
Presentations and Class Participation: Each of you will give a 20-30 minute presentation on the
assigned Thursday paper. Each of you will also lead discussion on the Tuesday problems. In addition, I
will ask you to go to the board regularly. Your class involvement will be part of your course grade.
Seminar Requirements: If your schedule allows (no TA duties) I expect all UMCP students to attend
Thursday seminars at 11 am, and the departmental seminars that are held at 3:00 pm on Fridays:
Fri, Jan. 28 Eric Anslyn, University of Texas
Fri, Feb. 11 Richard Schrock, MIT
Fri, Feb 25
Marc Greenberg, Johns Hopkins
Fri, April 8 Eric Kool, Stanford
Fri, April 22 Chad Mirkin, Northwestern
Fri, May 6
John Bercaw, Cal Tech
Grading:
1 Mid-Term Exam @ 100 points
100 points
1 Final Exam @ 100 point
100 points
2 Papers @ 50 point each
100 points
1 Research Proposal
100 points
Class & Seminar Participation
100 points
Total
500 points
After evaluation of scores I'll decide on a letter grade. I may use the +/- option in this class.