The University of Missouri at Columbia
Chemistry 212 - Organic Chemistry II - Winter Semester 2003

Professor Dr. Rainer Glaser
Office 321 Chemistry Building
Telephone (573) 882-0331
Chemistry 212 Course Web Site
Laboratory Preparation & Active Learning
MWF 9:00 - 9:50, 126 Physics
R 9:00 - 9:50, 126 Physics
First Lecture Wednesday, January 22, 2003
Office Hours WF 10:00-10:50

Course Goals

Organic chemistry is pervasive in every aspect of modern life. Chemistry is the central science and every science major needs to master chemistry. Many consumer choices, economic choices and political choices require the understanding and competent application of chemical concepts. Chemistry knowledge thus informs both the professional life of a science major as well as his/her life as good citizen in a democratic society. It is the goal of this course to teach students the abilities to ...

[1] Learn the (symbolic) language of organic chemistry.
[2] Develop clear conceptual ideas and quantitative knowledge about the sources, properties, reactions and uses of organic chemical materials.
[3] Access online journals and databases and extract information form these sources.
[4] Understand the historical context and the culture of the field of organic chemistry and to judge your own work and the work by others in that context.
[5] Read the contemporary press and media and learn to identify and place in context any issues which require an understanding of organic chemistry for their complete appreciation.
[6] Enable autodidactic behavior - the utopian goal.

Aristotle's World

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

The Modern World

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.

recognize building blocks and functional groups
recognize properties of fragments
connections between building blocks
polymerization of monomer
3d-stereochemistry of monomers & polymers
structure determination

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

Course Materials and Book Adoption Policy

I am recommending two books to you. The text by Carey is the text currently adopted by the MU Organic Chemistry Divison and this text is therefore the required text for this course. My course organization coincides with the organization of the book by Wade and some of you might find that text helpful as well.

Feel free to use any other text on Organic Chemistry. There is general agreement among all the books about the core curriculum at this level of chemistry instruction. Using several books or switching between books from one course to the next can, in fact, be an advantage. Getting another perspective is a positive experience. Comparing two texts emphasizes key areas and diminishes tangential issues.

For the purpose of testing and performance assessment, the course content is defined by the activities during regularly scheduled meeting times.

Course Materials I. Books and Model Sets.

(1) Required Text & Study Guide: F. A. Carey, Organic Chemistry w/ CD and Study Guide/Solutions Manual, 5th eddition, 2003, McGraw-Hill, Dubuque, IA. ISBN 0074174320. Cost: $ 150.75 (at MU Bookstore).

(2.1) Recommended Text: Organic Chemistry, Leroy G. Wade, Jr.; 5th ed., Prentice Hall, Upper Saddle River, New Jersey 07458, 1999. ISBN 013033832x. Cost: $102.70 (at MU Bookstore).

(2.2) Recommended Study Guide: Study Guide and Solutions Manual for Organic Chemistry, Jan W. Simek; 5th ed., Prentice Hall, Upper Saddle River, New Jersey 07458, 1999. ISBN 0130600288. Cost: $52 (at MU Bookstore).

(3) Required Model Set: HGS Molecular Model Set, C Set for Organic Chemistry, W. H. Freeman and Company. ISBN 0716748223. Cost: $32.

Course Materials II. Laboratory Teaching Materials.

Educational materials from various sources will be used in the laboratory. Some of the materials were developed by faculty of the Department of Chemistry while other materials are adopted from Chemical Education Resources. For your convenience, all of these materials are available in electronic format at the same location along with spectral information, grading information and so on. A password is required to access these files and you will be given that password in lecture.

(4) Required Laboratory Materials available at bookstore: Bound Chemistry 212 WS03 lab manual containing the CER experiments bundled with laboratory notebook. Cost: $21.00.

Course Materials III. Resources of the World Wide Web & The New York Times.

We will make extensive use of the world wide web as instructional tool. Chemistry is in the News activities, studies of Visualization Centers, explorations of Web Destinations, inspections of Reaction Animations all are web based.

As part of the "Chemistry is in the News" project, you are required to read The New York Times this semester. The New York Times is the Nation's newspaper and features a superb science section in its Tuesday edition. In fact, there are many articles in The New York Times every day that are in some way related to science in general and chemistry in particular. We want to learn to see these connections! In previous semesters, I have frequently based test questions on NYT articles and I will continue this practice. So, keeping up with the Times will be good for your chemistry grade. There are several ways for you to read The New York Times:

[a] Buy a subscription of The New York Times for $0.40 per day and pick it up every morning at the General Books Information Desk at the University Bookstore in Brady Commons. There is nothing like browsing the hardcopy! Subscription forms for WS03, M-F, 75 issues for $30, will be distributed in class at the end of the first lecture.

[b] Get your daily copy of The New York Times from one of the vending machines on campus.

[c] Read the online version of The New York Times and print out what you like.


I. Commitment

Chemistry 212 is a demanding course and a clear commitment has to be made. Merriam Webster's Dictionary defines (noun, 1621) as "a: an agreement or pledge to do something in the future; especially: an engagement to assume a financial obligation at a future date b: something pledged c: the state or an instance of being obligated or emotionally impelled (a commitment to a cause)."

Four hours of lecture and a four hour lab. For every hour of lecture, you are expected to spend two hours studying and you need at least another two hours to prepare and write-up the laboratory sessions. This means that you are expected to spend 8 hours every week studying for this course IN ADDITION TO the 8 contact hours. So, this course requires 16 hours of your time every week and this needs to be clear to you from the very start. And before tests you might want to put in a few extra hours on top of that. While this course is demanding, it also is very fair in that there will be clear expectations as to what you need to do. If you invest the time, you will do well.

Just coming to lecture and putting in a few hours before a test is a strategy that does not work in chemistry. There have to be a permanent effort and a planned commitment of time to spend on studying chemistry. Students often have difficulty with time management and this is a skill that needs training. Keep a time sheet, for example, and write down honestly what you studied at what time. "Interruptions" do not count as study time. We will have a "study habits" module in February.

II. Lectures

Come to class well prepared! Do read the material before it is covered in class. We want to spend considerable time "talking about chemistry" in class. After the lecture, read the material again and test yourself, possibly in small groups. If uncertainties remain, review the material again, talk to one of the teaching assitants, or come to see me during office hours.

III. Laboratory

The 4-hour laboratory session constitutes an essential part of Chemistry 212 and ten sections are offered. Experiments will be discussed in the Thursday lecture of the week preceeding the performance of the experiment. For details about the laboratory component of Chemistry 212, see In The Laboratory.

IV. Collaborative Group Activities

Chemistry is very much like a language. You need to learn the structures and the names of compounds and their properties. This is much like learning the spelling and the meaning of a new word in a foreign language. Then you need to learn the rules governing the reactions of these molecules. There is a grammar to chemistry just like there is grammar in language. Nobody would expect a language student to be able to speak the language after "attending lectures" and "studying the book." Of course not! A language is learned by "speaking in the language" and the same is true for chemistry. You need to put yourself in situations in which you "talk chemistry." It is the purpose of the Chemistry 212 Collaborative Groups to engage the students in collaborative learning activities and to train and develop their ability to work with their peers. Talking chemistry with your peers, working together on assignments, obtaining feedback obtained from your peers, all of these mechanisms will provide opportunities for more active learning, will create the framework for support and constructive criticism, and will teach you valuable lessons on group dynamics. You will have to think about the peer group rather than focusing on your internal standards alone.

We will partition the class into student groups of 4-5 students. The members of a group are required to be in the same laboratory section. Look to the members of your group to discuss problems you encounter in the lectures or in the laboratory, compare notes, discuss strategy in problem-solving ... and exercise your chemistry knowledge through these active learning activities.

The groups are self-selected and there are some obvious ways to form groups. Some of you might know each other from courses previously taken together, from living in the same dorm, engaging in the same sports, you might know each other from Greek Life, and so forth. Others might be new to Columbia and MU and might not know anybody in this course as yet. In either case, to find other students to create your groups just approach other students and ask whether they might be interested in joining you. A discussion list will be created within the first week of the course and the list can be used to announce any vacancies in your group or to inquire as to who might want you in their group. Practical aspects (where does (s)he live, what times is (s)he available, ...) are as important as personal matters (do you think you can get along with this student ...) and your estimate of his/her ability and motivation (is this student likely to contribute to the group ...).

Groups need to be formed by the end of the first laboratory week; Friday, January 31, 2003. Send an email note to Mr. Wu that contains in this order and on separate lines (a) the name of the group (be creative, come up with some interesting group names!) and (b) names and email addresses of the 4-5 group members.

V. Computer-Laboratory

You will engage in a variety of computer-assisted learning activities. These activities will include working with web-based teaching materials and hands-on molecular drawing and modeling. Instructions and introductions to these activities will occur in the Thursday lecture periods. You can pursue the web-based activities later on at any time from any place. The molecular drawing and modeling exercises require special software only available in the computer laboratory of the Department of Chemistry.

We recommend that you study the Visualization Centers in small groups. It is one of the aims of the web-based teaching materials to improve your understanding of structure and to begin to see how structure affects function. The Visualization Centers provide accurate structures of selected molecules in an online format. Each structure can be viewed from user-selected perspective and a mini-tutorial is provided for guidance. Talk about the minitutorials and talk about the structures displayed.

The establishment of relevance is an important co-factor in the learning process. An excellent way to establish the relevance of the content of Chemistry 212 is by way of connecting the course content to the real world. We will study Chemistry is in the News items to construct these connections between chemistry and society. These teaching materials are based on the philosophy that "newspapers mirror society and newspaper allow to construct the important relations between society and chemistry." There is one "news item" per chapter and it includes one published newspaper article, editorial comments, and questions. The editorial comment section often includes links to high quality sites on the world wide web.

Further guidance to WWW sites is provided by the Portal to Organic Chemistry on the World Wide Web. Ths collection of chemistry related links is permanently under construction. You are invited to tell me about sites you would like to have added.

Molecular drawing and modeling activities will make use of ChemOffice. ChemDraw is a structure drawing program and Chem3D is a versatile molecular modelling program. You will learn how to draw structures and include those in reports. You will learn how to find the "best" structure of a molecule and you can visualize the molecular orbitals and many other properties.

The materials covered in these web-based teaching materials and/or computer-assisted activities will be revisited in the tests. About 25 percent of each test will be concerned with these materials.

VI. Writing Assignments & Chemistry is in the News

As described above, we will study Chemistry is in the News items to construct connections between chemistry and society. In addition, you will be asked to create a new "Chemistry is in the News" item with your group as part of the Writing Assignments. There are three writing assignments and all of them will have to be carried out as group. The first and second assignments have to submitted for review, revised, and the revision will be graded by the instructor. The third and major writing assignment consists in the creation of one "Chemistry is in the News" item by each collaborative group. These online projects will receive constructive peer review and, after revisions have been made to address the peer commentary, they will be graded by peer review.

VI. Exercises

You are asked to work a selection of the problems in the textbook and the selection will be posted at the Chemistry 212 Course Web Site. You are not required to return the answers. You should work these problems on your own, discuss difficult issues and check answers with the members of your collaborative group.

VII. Meet Your Teacher

Every other week or so, there will be a Chem 212 lunch. These lunches will happen at the Memorial Union, at Hudson Hall, and at the Heidelberg. And once even at the University Club! Everybody is welcome!

Examinations and Grading

The Greek philosopher Socrates argued that the unexamined life is not worth living.

      Evaluated Examination or Activities   Points
      Exam 1 on                                50
      Exam 2 on                               100
      Exam 3 on                                50
      Exam 4 on                               100
      Exam 5 on                                50
      Exam 6 on everything!                   150

      Writing Assignment I                     50 
      Writing Assignment II                    50 
      Writing Assignment III (Group Project)  100 Inter-Group Peer Review
      Collaboration                            50 Intra-Group Peer Review

      In the Laboratory                       250 

      Course Total                           1000 

Grading is based on an absolute grading scheme to reward competency rather than competition.
        Grade A+ above 95%, grade A above 90%, grade A- above 85%, 
        Grade B+ above 80%, grade B above 75%, grade B- above 70%,
        Grade C+ above 65%, grade C above 60%, grade C- above 55%,
        Grade D+ above 50%, grade D above 45%, grade D- above 40%;  
        Grade F  less than 40%.  

In concert with the policy of the Department of Chemistry, there will be no make-up exams. 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 miss a test without a legitimate reason, you will receive a score of zero points for that test.

Relevant University Regulations

Final Examination. The final examination is scheduled for Monday, May 12, 2003, 8:00 - 10:00 am. Time and date of the final examination are determined by Article V of the Academic Regulations which are designed to protect students from irregularities in the administration of final examinations. The following two excerpts from Article V are relevant to this graduate class. (1) No teacher will hold an examination during any time other than the regular meeting time of the class or the time as approved by the Registrar for both final and multi-section examinations. The only exception is that examinations in courses numbered 400 and above may be conducted at any time agreeable to both the teacher and the students. (2) No examination may be held during Stop Day.

Academic Honesty. Academic honesty is fundamental to activities and principles of a university. All members of the academic community must be confident that each person's 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 student's Dean. (8/2/00)

Instructional Communication Policy. MU is determined to promote effective communication between students and academic personnel involved in instruction. To report communication problems with the instructor or the teaching assistants, please contact Dr. John Adams, Director of Undergraduate Studies, Department of Chemistry; e-mail:

Compliance with the Americans with Disabilities Act. If you need accommodations because of a disability, if you have emergency medical information to share with me, or if you need special arrangements in case the building must be evacuated, please inform me immediately. Please see me privately after class, or at my office.
To request academic accommodations (for example, a note taker), students must also register with Disability Services, AO38 Brady Commons, 882-4696. It is the campus office responsible for reviewing documentation provided by students requesting academic accommodations, and for accommodations planning in cooperation with students and instructors, as needed and consistent with course requirements. For other MU resources for students with disabilities, click on "Disability Resources" on the MU Home Page (upper right) or visit the Disability Services web site. (1/20/03)

Excellence is a Habit