Fall 2005
CHEM 315
SYNTHETIC ORGANIC CHEMISTRY
| R.D. Libby
213 Collier Ext. 1436 |
Class Hours
MWF 11:30 AM - 12:20 PM Problem Session: Tuesday 10:20-11:10 AM 200 CHS |
Office Hours
Mon. 12:30 PM -> 1:30 PM Tues. 11:30 AM -> 12:30 PM Wed. 12:30 PM -> 1:30 PM Fri. 10:15 AM -> 11:15 AM Or any time, just call X1436 |
TEXT: Guidebook to Organic Synthesis 3rd Ed. by R. K. Mackie, D. M. Smith and R. A, Aitken (MSA)
REFERENCE: Organic Class Notes and Any Introductory Organic Text and
Books on the
CHEM 315 shelf in 221 Collier.
COURSE OUTLINE:
I. Introduction: Basic Principles of the Disconnection Approach to Organic Synthesis
and review of organic reaction
types. MSA Chapts. 1, 2.1 & 3 - pp. 1-5 & 25-37
II. Specific Strategies:
A. Formation of Carbon-Carbon Bonds: Organometallics. MSA. Chapt. 4
B. Formation of Carbon-Carbon Bonds: Carbanions MSA. Chapt. 5
C. Formation of Carbon-heteroatom Bonds MSA. Chapt. 6
D. Ring Closures MSA. Chapt. 7
E. Reduction MSA. Chapt. 8
F. Oxidation MSA. Chapt. 9
G. Protective Groups MSA. Chapt. 10
H. Boron Reagents MSA. Chapt. 11
I. Phosphorus Reagents MSA. Chapt. 12
J. Silicon Reagents MSA. Chapt. 13
K. Selenium Reagents MSA. Chapt. 14
L. Asymmetric Synthesis MSA. Chapt. 15
This course will be run in a group discussion manner. The
value of class periods is largely dependent upon what each student
contributes. Each new topic or concept will be presented to you
as an activity, which may include data to analyze, information to
recall or look up, and some questions to guide your work. You
will be required to work as a group, both inside and outside of class,
to devise what you believe to be reasonable responses, interpretations
or other analyses. Each day I will solicit your responses to each
part of the day’s activity. We will then discuss these initial
analyses or interpretations and try to identify the strong and weak
points of the proposals. Ultimately we will agree on approaches
that provide us new insights into the logic and process of designing
and carrying out efficient syntheses of organic molecules. Our
initial conclusions will then be tested through their application to
additional syntheses. Applications will sometimes be done as a
group in class, and other times will be out of class work
assignments. As the semester progresses, you should begin to
develop a personal "sense" of synthetic organic chemistry that will aid
you in each subsequent activity. I believe that you will find the
group discussions very useful in your learning process. In
general, this class is designed to simulate the way many scientists
actually work to design new synthetic processes; it is usually a group
effort. The course structure encourages you to take
responsibility for and an active part in your education in the area of
synthetic organic chemistry. Educational research indicates that
students who are actively involved with peers as they work on class
material, as you will be, tend to learn more in their courses and
retain more in the future. I hope that you will find that working
with your classmates will help in generating new ideas and provide you
better insight in your analyses of the daily activities. We will
have a class website (http://www.chem.moravian.edu/~rdlibby/chem315-05.html) to aid you in your out of class work, and much of the course material will be posted there.
| Quizzes | 15 % |
| Mid-term Take-Home Exam | 20 % |
| Library Projects | 20 % |
| Group Work | 20 % |
| Final Synthetic Proposal | 25 % |
Quizzes:
There will be short individual in-class
quizzes each week. The quizzes are designed to provide some encouragement
for everyone to get involved in the group activities and stay up with the
development of new synthetic methods throughout the semester.
Mid-term Take-Home Exam:
There will be a single Mid-term
exam. It will be a take-home exam to be given out on Monday
October 17 with your answers to be due by 5:00 PM on Monday, October
24. You may work alone or with your classmates to devise answers to the questions. However, you should write the final copy of your exam without direct consultation with others on the wording
(NO CARBON COPIES). In short your submitted answers are to be
your own understanding of the material based on work in class and
discussions with classmates.
Library
Projects:
There will be two opportunities for
you to select and analyze original articles on synthetic organic chemistry.
Group Work:
As explained in the group description and
duty
assignments given below, at the end of each class, the group managers
and reporters will submit reports on the groups' activities for the
day. The
reports include group responses to specific questions on the day's
activity sheet and one or more specific comments or questions the group
has about
the activity and/or class conclusions from the material being
considered. Daily group reports and contributions to class
discussion will determine each student's "group work" grade. This
grade is designed to recognize and reward individual contributions to
group discussions.
A Proposal for the Synthesis of an Interesting Organic Molecule
The final requirement for this course
is to submit an original proposal for research on an appropriate synthetic
problem.
Group Composition and Dynamics: In class, each day each member of the group has a specific role to play in making your collective learning experiences profitable. The duties associated with the specific roles are described below. Every day every member of the group will be assigned a new role.Class Groups
Group Role Definitions:
Manager
Manages the group. Insures that the group has the appropriate materials (textbook, molecular models, outside reference materials, etc.), that members are fulfilling their roles, that the assigned tasks are being accomplished on time, and that all members of the group participate in the activities and understand the concepts. The Manager communicates with the instructor when information or assistance is required and is responsible for seeing that group reports are submitted in a timely manner. Also, the manager completes the group’s Response Report with group members’ names, roles, and general comments and questions concerning the day’s activities
Recorder
Obtains the group folder and records group answers and explanations,
along with questions the group has in dealing with the material.
Submits the group records to the instructor with the group folder at
the end of each class period. The Recorder's answers will be
considered to be the official group response to each day's
activities.
Presenter/Reflector
Presents group conclusions when requested by the instructor.
These presentations may be oral or written on the blackboard, and will
be the basis for day’s discussions. Also, observes and comments (reflects) to the manager on group dynamics and behavior
with respect to the learning process, and the effectiveness of the
group in dealing with daily assignments. This group member may be
called upon to report to the group concerning how well the group is
operating or what needs improvement and why. For each class the
Presenter/Reflector completes a Reflector’s Report with an assessment
of the group’s performance for the day. The assessment has three
specific parts:
1. A strength of the group’s collaboration on the class group activity and why it was a strength.
2. An improvement that would increase the group’s success and how it might be accomplished.
3. An insight the Reflector had from observing the group interactions on the day’s activity.
INITIAL ROLE ASSIGNMENTS: For the first class period,
group roles will be assigned alphabetically by the last names of group
members. 3rd alphabetically will be the Manager, 2nd alphabetically will be the Recorder, 1st alphabetically will be the Presenter/Reflector.
ROTATION OF ROLE ASSIGNMENTS: The role rotation order between classes is Presenter/Reflector becomes the next Recorder, the Recorder becomes the next Manager and the Manager becomes the next Presenter/Reflector.
(i. e. Presenter/Reflector -> Recorder ->Manager -> Presenter/Reflector)
The following books are on the CH 315 shelf in 221 Collier
Angewandt Chemie International EditionAsymmetric Organic Reactions, by James Morrison and Harry Mosher, 1971 (QD262 .M74)
Biotransformations in Organic Chemistry: a textbook, 3rd ed., Kurt Faber, 1997 (TP248.65.E59 F3 1997)
Compendium of Organic Synthetic Methods, Vols. 1-3, by I. T Harrison, 1971 (QD262 .H32)
Concepts of Organic Synthesis, by Bradford Mundy, 1979 (QD262 .M79)
Functional groups: characteristics and interconversions, by G. Denis Meakins, 1996 (QD251.2. M435 1996)
Organic Synthesis by Michael B. Smith, 1994 (QD262.S65)
Organic Synthesis: Concepts, Methods, Sarting Materials, 2ndEd., by Jürgen Fuhrhop and Gustav Penzlin, 1994 (D262 .F78 1994)
Science of Synthesis: Houben-Weyl methods of molecular transformations, 4th ed., 2000 (QD258 .S35 2000)
Selected Organic Syntheses: A guidebook for organic chemists, by Ian Fleming, 1973 (QD262 .F58)
Survey of Organic Synthesis, vols. 1 & 2, by Calvin Buehler and Donald Pearson, 1976 (QD262. B78)
The logic of Chemical Synthesis, by E.J. Corey and Xue-Min Cheng, 1995 (QD262. C577 1995)
Why poison ourselves: a precautionary approach to synthetic chemicals, by A. P. McGinn, 2000 (RA1226 .M24 2000)
Organic Synthesis Reaction Guide, vols. 1-7, by Dennis Liotta (QD262 .O72 Guide)In addition, the following reference series are in the stacks at Reeves Library.
Organic syntheses, vols. 21-26 and 41-74, by Roger Adams (QD262. O7)
Reagents for Organic Synthesis, vols. 2-8, by Louis Fieser and Mary Fieser (QD262 .F5)
Journals with Significant Synthetic Material
In Reeves LibraryJournal of the American Chemical Society
Journal of Organic Chemistry
Synthesis
TetrahedronIn Lehigh Chemistry Library (Fairchild)Tetrahedron Letters