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© 1996, 1997 Rainer Glaser. All rights reserved.

The University of Missouri at Columbia
Chemistry 210 - Organic Chemistry I - Winter Semester 1997

Organic Chemistry
A Brief Introduction By Example

A very simple piece of DNA is shown. Understanding DNA is of interest to many areas including Chemistry, Biochemistry, Biology, Medicine, ... and of course Philosophy. To begin to understand anything about this very special molecule we need to analyze the molecule and then test hypotheses we have come up with.

nomenclature
recognize building blocs and functional groups
properties of building blocs and functional groups
connections between building blocs
polymerization of monomer
3d-stereochemistry of building blocs, monomers, polymers
structure determination

The Four Pillars of Modern Chemistry

In the modern view of chemistry, Experimentation, Theory & Computing, and Data Analysis are the three equally important sources of hypotheses and their testing grounds. The fourth pillar comprises the ensemble of Learning Methods.

About Learning in Customary Educational Settings

Similarly, no one has been able to confirm any certain limits to the speed with which man can learn. Schools and universities have usually been organized as if to suggest that all students learn at about the same rather plodding and regular speed. But, whenever the actual rates at which different people learn have been tested, nothing has been found to justify such an organization. Not only do individuals learn at vastly different speeds and in different ways, but man seems capable of astonishing feats of rapid learning when the attendant circumstances are favourable. It seems that, in customary educational settings, one habitually uses only a tiny fraction of one's learning capacities. [ Emphasis ours]

Excerpt from the Encyclopaedia Britannica

Complexities of Human Learning

Human learning is complex rather than simple. Learners are apt to learn more than one thing at a time. Sometimes this process is conscious, as when one simultaneously or rapidly assimilates many specific items of a whole. More often, the process is entirely or partly unconscious, as when the student learns some "content" consciously but at the same time absorbs unwittingly a great deal more from interrelationships, tones of voice, and so on.

Educators are therefore becoming increasingly concerned with these concomitant learnings. They are aware that the long-term significance of the arithmetical skill that the student consciously learns may be nugatory compared with the importance of what he learns about himself as a learner, about his capacities and limits, about his relationship with his teacher, about power and authority, about his relationships with his fellow students, about equality, collaboration, competition, and friendship. As educators become more knowledgeable about the importance of learning climates, they are impelled to abandon simplified techniques of teaching in favour of a more complex approach that views learning in the context of a matrix of relationships and forces that act upon the student, the teacher, the school, and the community.

Excerpt from the Encyclopaedia Britannica

Aristotle's World

Aristotle (384-322 BC) was very wrong ... we are getting better but beware!

Course Materials I. Books and Model Sets.

(1) Required Text: Organic Chemistry, Vollhardt, K. Peter C.; Shore, Neil E.; 2nd ed., W. H. Freeman and Company, New York, 1994. ISBN 0-7167-2010-8. Cost: $76 text only; $92 text plus study guide.

(2) Optional study guide: Study Guide and Solutions Manual for Organic Chemistry, Schore, Neil. E., 2nd ed., W. H. Freeman and Company, New York, 1994. ISBN 0-7167-2572-X. Cost: $30 study guide alone.

(3) Recommended (highly) model set: HGS Molecular Model Set, C Set for Organic Chemistry, W. H. Freeman and Company. ISBN 0-7167-1972-X. Cost: $24.

(4) Potential Study Option: Organic Nomenclature - A Programmed Introduction, Traynham, J. G., 5th Ed., Prentice Hall, Upper Saddle River, New Jersey 07458. ISBN0-13-270752-7. Cost: $26.

(5) Potential Study Option: Pushing Electrons - A Guide for Students of Organic Chemistry, Weeks, S. P., 2nd Ed., Updated version, Saunders College Publishing, Harcourt Brace & Company, 8th Floor, Orlando, Florida, 32887. ISBN 0-03-011652-X. Cost: $16.75 (net).

(6) Potential Study Option: Electron Flow in Organic Chemistry, Scudder, P. H., John Wiley & Sons, New York, 1992. ISBN 0-471-61381-9. Cost: $__ (net).

Course Materials II. Software Options.

An attempt is made at integrating computer software for molecular drawing, modeling & visualization, and review & self-studying into Chemistry 210 for the first time. Inside and outside of the classroom, we will make extensive use of the world wide web as a tool for instruction. If you are enrolled in the honors' section of this class, you will have the opportunity to become involved in the design of computer-assisted exercises. You will also have the opportunity to write chemistry software reviews.
The following software pieces will be used in some fashion during the course. Some of you might want to purchase this software for use at home or on some of the computers in the Campus Computer Laboratories. Consider buying the software with two or three friends; share the cost and share the fun of learning.

(1) Recommended computer tutorial: Organic Chemistry: Reaction Mechanism. Authored by Montana and Buell. Distributed by Falcon Software. MAC ISBN 1-886959-05-6. WIN ISBN 1-886959-06-4. Suggested student price US$ 39.95.

(2) Recommended computer tutorial: Organic Chemistry: Spectra of Compounds. Authored by Schatz. Distributed by Falcon Software. MAC ISBN 1-886959-08-0. WIN ISBN 1-886959-09-9. Suggested student price US$ 39.95.

(3) Recommended drawing & modeling software bundle: Organic Chemistry Survival Kit. Distributed by Saunders College Publishing, Harcourt Brace & Company, 8th Floor, Orlando, Florida, 32887. MAC: ISBN 0030 200 326. WIN: ISBN 0030 200 327. Cost: $39 net.
This bundle contains ChemOffice Ltd. 3.1 and the Saunders Interactive General Chemistry CD-ROM. The ChemOffice Ltd. 3.1 contains the drawing program ChemDraw and the modeling program Chem3D. The CD-ROM is a set of two CDs and comes with a 300-page book. A nice review piece!

Prerequisites

You should be familiar with the concepts and principles discussed in general chemistry, that is, having passed Chem 32 with a grade of C- or better. Students who have had Chem 115, 205, Biochem 110 or equivalent can receive only 1 hour credit in Chem 210.

Lectures

It is very important that you come to class well prepared! Do read the background material before it is covered in class. The lecture will be much more beneficial to you if you do. One of the advantages of being well prepared is simply that you need to write much less during the lecture and, instead, you will be able to follow the lecture intellectually. After the lecture, read the material again and test yourself, possibly in small groups. If uncertainties remain, review the material again or come to office hours.

Discussions - Reviews

If necessary and desired, discussion/review sessions will be scheduled in the evening in order to fit in with your schedules. These sessions are intended to serve three purposes: First, further discussion of the more difficult topics presented in class (not additional material), secondly, discussions of problems, and - most importantly - general Q&A and problem solving strategies. Dates will be announced in class as required.
To encourage discussions amongst yourselves, you will be subscribed to a Chemistry_210 discussion list. There will be several lists to keep the number of subscribers low. Details about the discussion lists will be given in lecture.

Examinations and Grading

There will be three 1-hour-examinations (100 points each), a group project (100 points), and a comprehensive final (200 points). The 1-hour-examinations will focus on the materials covered recently, but it is expected that you recall the fundamentals of previously studied chapters. Purpose and details about the group projects are described on a separate web page. There will be no quizzes.

No grades will be assigned to individual tests. After each examination you will be given a graph representing the performance of the class that will enable you to assess your relative performance. The tests are fair but they are not easy and they are not short either. Performance is work divided by time and performance is tested. The philosophical basis is simple: If you do not know the material now so well that you can answer quickly, then you will not know the material at all in a year from now. The goal is learning for long-term retention. In the past, averages have been between 45 and 65 points out of 100 possible points and achieved individual scores have varied from about 15 all the way up to the low 90s. Remember that your grade will depend on your relative position with regard to the average. A score of 70, while seemingly low, is still an A grade if the average is about 50. Remember also that this type of testing strategy allows for two important advantges: First, you can obtain a very good grade even if you decide to focus on some material more than on others (you do not need 95 points for an A!). Second, this method of testing makes it much more possible to make up for a test you may have blown completely (with class averages of 90, you would never be able to make up for one bad performance that left you 20 under par!). Thus: While you might not feel too happy about the low averages and your low point counts, you should realize that this system actually works in your favor. In the best of all possible worlds, I would hope that we would achieve averages of 65 - 75 points for the 100-point exams. At that level of performance, you could compete with just about anybody.

After completion of all 1-hour-examinations and of the group projects and before the final examination, you will be informed regarding the point/grade relation. Grades are assigned based on the average of the class and the class distribution. In a previous semester, for example, with a course average of 59 percent, the following cuts were used: Grade A (14.9%) above 76 %, B grade (22.6%) above 64 %, C grade (35.1 %) above 50 %, and so on. Plus/minus grades will be given within this framework. A+ for the top 3 percent. You can check out the histograms and grade assignments for Chemistry 212 from the Fall Semester of 1996 to see how this all works out.

In concert with the policy of the Department of Chemistry, there will be no make up exams. If a test is missed for a legitimate reason (sickness and the like with some type of acceptable written proof), a score will be determined for this missed test that is based on your average overall performance. If you know in advance, that you will not be able to take an exam for a certain reason, talk to the instructor before the date of that test. If you do miss a test without a legitimate reason, you will receive a score of zero points for that test.

Honors

An honors' section is available. You can earn honors credit through the learning-by-contract option offered by The Honors College. Please refer to the Guidelines for Honors Learning-By-Contract to learn about the administrative aspects. Get a Learning-By-Contract Form from the Honors College and come to see the instructor to discuss the options for the project.

Option (1): Attend six Chemistry Colloquia (Fridays, 3:40, Schlundt 103), write brief summaries of the presentations (one page or less), and hand this report in. Option (2): Research an area of your interest related to organic chemistry and write a term paper on it (5-7 pages, double spaced). Option (3): Explore computer-assisted learning methods and design an exercise. I favor options (2) and (3). If you would like to pursue either option, get the required forms from the Honor's College and see me for advice & approval.

As far as option (2) is concerned, topics that have been selected in the past include, for example, DNA finger printing, alternative fuel sources, ozone depletion and so on. I'd be more than happy to help you with your topic selection and to provide guidance (e.g. literature). Topics that reflect the impact of chemistry on modern society are encouraged. You might get some ideas from the New York Times Science pages or from the Science department of Time magazine.

Option (3) relates to the integration of computer-assisted learning into Organic Chemistry education. You will be involved in testing and developing computer-assisted review and self-study exercises. A typical honors' project would consist in the complete production of one exercise segment from the conception of an idea to writing the student guide to the exercise. If you choose this option, I will instruct you in the usage of software (ChemDraw, Chem3D, MacSpartan) which you can apply to the design of your exercise. I think this is the most interesting and exciting option and you will certainly learn a great deal about chemistry and about computer-assisted teaching & learning technology.

Academic Honesty

Academic honesty is fundamental to activities and principles of a university. All members of the academic community must be confident that each personŐs work has been responsibly and honorably acquired, developed, and presented. Any effort to gain an advantage not given to all students is dishonest whether or not the effort is successful. The academic community regards academic dishonesty as an extremely serious matter, with serious consequences that range from probation to expulsion. When in doubt about plagiarism, paraphrasing, quoting, or collaboration, consult the course instructor. Proven academic dishonesty will be reported to the Provost for Academic Affairs and the studentŐs Dean.