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

CLASS FORMAT

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.


ADMINISTRATIVE POLICIES
Missed Exam or Quizzes:
Students are required to take all exams and quizzes.  There will be NO MAKE-UPS.  If an exam or quiz is missed without a valid medical excuse (verified by the Health Center) or other accepted prior excuse, the grade for that work will be zero.  The grade for an exam or quiz missed due to an excused absence will be determined from the grades earned on the remaining exam(s) (including the final exam) or quizzes, i.e. more value will be added to subsequent exams or quizzes.  The final exam will be given at the time specified by the registrar during the final exam period.  Make-up finals for those with verified conflicts will be given on the last day of the final exam period.

NOTE:    Travel schedules for weekends or breaks are not acceptable excuses for missing quizzes, exams, lab discussions or lab periods.

Collaboration and Academic Honesty:
Collaboration among students in class and in preparation for class discussion is generally encouraged and required for most classes.  Educational research indicates that students learn best when they engage in discussions and analyses of class material with their peers.  However, the final version of all written work submitted for evaluation must be prepared without consultation with other students.  To be fair to all students in the course and to assure maximum learning for each student, we follow all the guidelines for academic honesty spelled out in the Moravian College Student Handbook 2002-2003 (pages 50-56).  Particularly relevant passages are excerpted below.

Academic Honesty at Moravian College
Academic integrity is the foundation on which learning at Moravian College is built. Moravian College expects its students to perform their academic work honestly and fairly. In addition, a Moravian student should neither hinder nor unfairly assist the efforts of other students to complete their work successfully. The College's expectations and the consequences of failure to meet those expectations are outlined below.

In an academic community, students are encouraged to help one another learn. In fact, because no two students learn in exactly the same way or take exactly the same things away from a lecture, the College encourages students to study together. The boundaries on what is or is not acceptable work may not always be clear; thus, if at any point in academic work at Moravian the student is uncertain about his or her responsibility as a scholar or about the propriety of a particular action, the instructor should be consulted. The list below is not to be considered complete but rather covers the most common areas of concern. In general, students should be guided by the following principles.

Plagiarism
A major form of academic dishonesty is plagiarism, which the College defines as the use, whether deliberate or not, of any outside source without proper acknowledgement. While the work of others often constitutes a necessary resource for academic research, such work must be properly used and credited to the original author. This principle applies to professional scholars as well as to students. An "outside source" is any work (published or unpublished) composed, written, or created by any person other than the student who submitted the work. . . .  All work that students submit or present as part of course assignments or requirements must be their original work unless otherwise expressly permitted by the instructor. . . .  When students use the specific thoughts, ideas, writings, or expressions of others, they must accompany each instance of use with some form of attribution to the source. Direct quotes from any source (including the Internet) must be placed in quotation marks (or otherwise marked appropriately) and accompanied by proper citation, following the preferred bibliographic conventions of the department or instructor. . . .  Student ignorance of bibliographic convention and citation procedures is not a valid excuse for having committed plagiarism. . . .  A student may not present oral or written reports written by others as his or her own work. . . .  You may not use writings or research obtained from any other student previously or currently enrolled at Moravian or elsewhere or from the files of any student organization (such as fraternity or sorority files) unless expressly permitted to do so by the instructor. . . .  Students must keep all notes, drafts, and materials used in preparing assignments until a final course grade is given. . . .  All such materials must be available for inspection by the instructor at any time. 

Cheating
Students may not submit homework, computer solutions, lab reports or any other coursework prepared by, copied from, or dictated by others. If the student is employing the services of a tutor (whether from the College community or elsewhere), the tutor may not prepare the student's work for class.

Students may not provide or receive unauthorized help in taking examinations, tests, or quizzes or in preparing any other performance requirements for a course. Such restrictions are illustrated by but not limited to the following: Using unauthorized material in an examination, test, or quiz.
False Testimony
Students may not submit or present a falsified excuse for an absence from an examination test, quiz, or other course requirement either directly or through another source.
Students may not falsify laboratory results, research data, or results. They may not invent bibliographical entries for research papers, websites, or handouts. They may not falsify information about the date of submission for any coursework.

EVALUATION

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. 

Final Project:

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.
 

Class Groups
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.  

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)


Library Reference List
The following books are on the CH 315 shelf in 221 Collier
(Please use them there and leave them for others.)

Asymmetric 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)

 

In addition, the following reference series are in the stacks at Reeves Library.

Organic Synthesis Reaction Guide, vols. 1-7, by Dennis Liotta  (QD262 .O72 Guide)

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 Library
Angewandt Chemie International Edition

Journal of the American Chemical Society

Journal of Organic Chemistry

Synthesis

In Lehigh Chemistry Library (Fairchild)
Tetrahedron

Tetrahedron Letters