INDEX TO THIS SYLLABUS

SCHEDULE OF TOPICS

1.Texts and Other Materials

1. Required:
1. Organic Chemistry, John McMurry, 6th edition, Brooks/Cole Publishing (ITP), Pacific Grove, 2004. Includes stereoviewer.
2. Supplementary Enrichment Materials Required for Organic Chemistry I, L. M. Sweeting, 1998 (downloadable free from the WWW: see schedule for links)
2. Recommended:
1. Study Guide and Solutions Manual for McMurry 's Organic Chemistry, 6th ed Susan McMurry, Brooks/Cole (ITP), Pacific Grove, CA, 2004. Solutions to problems in the text, not just answers. self-tests, multiple choice questions (prepare for professional school tests!), chapter outlines.
2. Organic Chemistry OnLine 2.0 Workbook to Accompany McMurry's Organic Chemistry, 5th edition, Paul R. Young, Brooks/Cole Publishing (ITP), Pacific Grove, 2000. Additional problems like some I will use for quizzes and exams.
3. Exams for Organic Chemistry I, L. M. Sweeting, 1997 (downloadable from the WWW; see schedule for links)
4. Organic Reaction Summaries and Quizzes available free from my WWW Organic Chemistry home page along with links to other WWW resources on nomenclature and reactions. Use these on-line as a review. Preparing your own summary will help you learn more and save trees (see "Secrets" below).
5. Molecular Models (a,b,c,d usually available at TU)
1. Flexible StereoChemistry (Darling Models) - I use these. Some assembly required.
2. Organichem (Freeman) - cheap and compact but flimsy
3. Molec. Model Set (Allyn & Bacon) - elegant-looking but clumsy for double bonds.
4. HGS (Benjamin) - clumsy for double bonds, otherwise good, very compact
5. Prentice Hall - metal jacks and plastic tubes. Some assembly required.
6. Theta (John Wiley) - cheap but flimsy.
7. See also web links for stereochemistry
6. Learning Objectives and Study Guide by L. M. Sweeting, referred to above as LOSG and available free on the WWW via link from http://www.towson.edu/~sweeting/orgmap.htm. Suggested problems and a list of "things you need to know".
7. Practical Spectroscopy: The Rapid Interpretation of Spectral Data for McMurry's Organic Chemistry 5e, Paul R. Young, Brooks/Cole Publishing (ITP), Pacific Grove, 2000.

2. Some Secrets to Success

Organic Chemistry has the reputation of being a very hard course, requiring a lot of memorization. There is no question that it will challenge your organizational skills, but your instructor is evidence that it is possible to succeed without a photographic memory. Be forewarned, though: it is not possible to succeed in Organic Chemistry without good study habits. The three secrets are: never get behind, practice, and always think about why the reactions occur. One more -- use the resources that are available to you.
Initially, the course will concentrate on language and structure, then will emphasize organic compounds with single bonds and their reactions. For structural principles, we will use physical models, pencils and computers; the nomenclature is systematic and can be learned with practice. To learn the reagents and products of reactions, some memorization will be necessary, and I will provide hints for learning the reactions. If you concentrate on why reactions occur, remembering what reactions occur will be easier to understand and learn. There are many facts to be learned in Organic, but they all fit very nicely into a theoretical framework that makes the learning much easier.  My lectures will focus on the information found in the text; I will emphasize the experiments and reasoning behind the mechanisms more than the text does. Although I may be a little ahead or behind the schedule above, I will discuss the topics in the order listed. "Reading Assignments" mean that you should read the chapters and the enrichment materials ahead of time: you won't understand everything, but you will learn much more in the lecture classes and will be able to formulate questions whose answers can really help you. Topics emphasized in class (relative to the book) will be those which merit extra time because of difficulty or importance. The enrichment materials will assist you in your learning and help relate organic compounds to your other courses and interests.
I have prepared an extensive web site linked to my Organic Chemistry home page which is used by students around the world to learn organic chemistry; check it out early and often. The site includes all the enrichment materials, the lecture syllabi for CHEM 331 and 332, summaries of all the reactions and drill quizzes (with answers), learning objectives, and links  to other sites with featuring stereochemistry, nomenclature and mechanisms. In addition, it includes laboratory syllabi, safety information and links to spectroscopy sites.
In addition to using the text and web resources, you need to study actively, writing summaries and working problems - the more of your senses you involve in the study process, the better you will retain information. I strongly recommend that you make reaction summaries (beginning with Chapter 6 in McM), either on flash cards or on sheets of paper, as an aid to learning reactions (details are found in the introductory study tips in LOSG). Your summary might be graphical or in the form of a list (see the WWW Reaction Summaries and Quizzes for one way); if you have ever made a concept map, you can use that too. Do not buy commercial flash cards or copy the summaries in the text - the main value in flash cards and other study aids is the thought that goes into preparing them. In fact, the best way to prepare your review materials is to try to prepare them from memory, then check against the text and notes, revising as needed.
It is not possible to learn Organic Chemistry without doing problems. From the beginning of the semester, set aside time each week for doing Organic problems, combining problems with analysis of the text and notes. Some people rewrite their notes, or make their summaries during their review and problem-solving sessions. I have recommended problems in the LMS Learning Objectives and Study Guide. The other problems are just as good and just as important; I chose a small set to ensure that if you are short of time, you do some of each kind. In addition, the Learning Objectives and Study Guide contains lists of "things you need to know"; because the Guide is textbook-independent, it is organized somewhat differently from your text and may include some things that are not in your text. You are responsible only for the information in your text and lectures, your laboratory curriculum and the enrichment materials provided.
The problems in the text are very much like those you will be asked to solve on exams, so use these as drills and practice tests. Links are provided in this syllabus on line to sample exams, using my previous exams. Because the precise scheduling of topics and exams varies somewhat from year to year, don't expect the scope of the archived exams to match precisely this semester's coverage.
During the semester, I will be improving the summaries and study aids. If you find any errors, please let me know ASAP so I can correct them. If you find any other sites that I should know about, please let me know and I will add links to them as well.

3. Problem Sessions and Quizzes

I will take one class per week for questions and problem-solving (by students in groups, with my help) if the classroom geometry makes it possible. This session was very popular with the students in spite of the extra work involved. Extra work? Yes, because I can only discuss two-thirds of the information in the text in class (the most difficult and most important, of course); the remaining one-third will be your responsibility. I plan to have the problem sessions Monday, on either the previous or the next topic (see Reading Asignment), but the pattern flexes with the content. You will get the most out of these problem sessions if you have reviewed your text and notes and worked some problems beforehand. If you spend most of the problem session looking up things in your text or notes, you will have wasted the opportunity to work problems with a coach or a collaborator at your elbow. I have placed reading assignments in the schedule on page 1 so that you can always be prepared. Many students have developed study groups from these problems sessions. Such study groups can be very helpful - students compare notes and problems, quiz each other, formulate questions for me, etc.

    If there is no problem session, I will most likely give a quiz on Monday.  The quizzes will be short (5 - 10 minutes), and will be discussed immediately and returned the next class.

4. Grading and Examinations

There will be three exams during the term plus a cumulative final.   In addition, quizes will be given regularly.   The exams will examine your understanding and recollection of the chemistry included in your text plus any additions or subtractions I make in class; the LMS Learning Objectives and Study Guide is more complete and some things in there will not be on the exams because they are not covered in your text or enrichment materials. My policy about attendance, etc. is explained in Section 7, Ethics. All of the questions on exams will require you to write, draw, outline or otherwise tell me what you understand about organic chemistry; there will be no multiple-choice questions and few choice or matching questions. Because of the kind of questions I ask, and the way I grade, the averages on tests will usually be about 65%, a C grade. The correlation of numerical grades with letter grades is as follows:
88-100% A Superior
75-87% B Good
55-74% C Satisfactory
50-54% D Less than satisfactory (credit except toward major)
0-49% F Unsatisfactory (no credit)

The bottom third of each range will be used for "-" grades and the top third for "+" grades. For example, the A- range will be approximately 88 - 91.
The final grade will be based on a weighted average of laboratory 35%, quizzes 5%, lecture tests 30%, and final exam 30%. Each student must pass both lecture and lab to pass the course. A student with a borderline grade who improves throughout the semester may get a higher grade than a strict average would predict, but not higher than another student with the same average.

5. Laboratory

A separate lab syllabus with a schedule and guidelines on safety and attendance will be distributed. The laboratory experiments correlate roughly with the lecture, and will introduce you to some of the practical problems in actually carrying out the reactions you meet in lecture. You are expected to be prepared by studying the experiment ahead of time and planning what you are going to do. Studying is not the same as reading -- you need to visualize doing things so that you will know what containers you need in what order, for example. Poor preparation is dangerous to your health and everyone else's. And don't forget to bring your notebook, goggles and text each time to lab -- you will not be allowed to work without them.
Spectroscopic methods of identifying the structure of compounds, discussed in McMurry Chapters 12 and 13 and outlined in LOSG II will be discussed primarily in the laboratory. Detailed examination will also occur on laboratory exams. However, questions on lecture exams and discussions in lecture will also include spectroscopy, since I place a stron emphasis on"how do we know?".

6. Sources of Help

1. Text and Study Guide. Don't look up the answers until you have tried the problems, and never just look up the answers - examine and try to understand the reasoning.
2. Instructor. Please see me during office hours; if you stop by without an appointment at other times, I may be able to help then, but I may have other duties that prevent me from doing so. You can reach me by e-mail, but I don't always have time to check my e-mail every day.
3. Tutor, Liina Ladon and assistants (Smith 538). Software available in the tutoring center, especially Orgtutor and RxDriller and internet access to WWW quizes.
4. Internet. Most of the course is summarized, with interactive problems, on my Web site, which also has links to other excellent sites; start with my Organic Chemistry home page and check out the Enrichment Materials, Reaction Summaries and Quizzes, Learning Objectives and Study Guide and Internal and External Web Resources. Don't be shy about checking around to see who else has put organic chemistry course information on the Web; let me know if you find any great new ones.
5. Other students:
1. in the class. You will be surprised how much working together on problems and summaries can help. Be careful not to sit next to your study partners on exams in case you have suspiciously similar answers.
2. students who have completed 331-332
3. upper division Chemistry majors
6. Old exams which are available on this web site through links from the schedule above. Please note that the content of exams varies somewhat from year to year with textbook and course pacing, but the style remains pretty much the same.

7. Ethics for Students in Organic Chemistry

Most students are never too sick to take an exam and never consider copying anyone else's work. I assume that students are honest and responsible in their work and will assume innocence until my suspicions are aroused. So that you will know what your rights and responsibilities are, I have explained below my policies on attendance and cheating.
1. ATTENDANCE in lecture is optional; however the student is responsible for learning what is discussed and the time and place of all tests (test dates and content are announced in class).
2. ATTENDANCE is required for all laboratory periods (lecture and activity) and tests. Any student arriving late for laboratory lecture may be denied permission to work in the lab for safety reasons; makeups may not be possible.
Students who are ill (or whatever) and cannot take a test or laboratory may be given a makeup opportunity if they i) inform me the day of the test of the reasons for their inability to appear and ii) supply a note from the doctor, mechanic, etc. attesting to these reasons -- before being considered for a makeup. Forgery of such documentation is equivalent to cheating on the exam or lab. Makeups are a privilege, not a right: they will be given only if scheduling can be arranged and they will be more difficult than the original. Anyone failing to appear for a makeup exam or lab (except as described in i) and ii) above) will forfeit the privilege for that time and for future times in this course.
3. CHEATING - Any work copied from a book or journal or another student without reference will be considered plagiarized and no credit will be given for the work it is part of. Extensive paraphrasing will receive the same treatment. Please remember this when you are writing lab reports and answering problem sets! Although consultation between students in solving problems is encouraged, identical problem sets will be considered plagiarized and will be given no credit. If others helped you solve the problems, give them credit - credit for assistance is a time-honored tradition in science.
Any cheating on exams (copying from each other or from materials brought in, substitute examinees, changing answers after tests have been returned, stealing tests, etc.) or in laboratory (results invented, fudged, doctored, copied, etc.) will result in a grade of F for the course. Without honesty, there is no science - there can be no compromises at any stage.
A note to all students about what constitutes cheating. In many ways the activities forbidden and called cheating in school (at all levels) are different from those which are forbidden in the workplace. For example, collaboration on projects is encouraged in the workplace, but usually forbidden in school. In this course, collaboration will sometimes be encouraged in laboratory, so that you can learn and practice the skills you will need in the workplace. This sometimes creates confusion about what is cheating. On the other hand, most cheating in school is also defined as cheating in the workplace -- taking credit for other peoples' work, inventing or altering data, for example. I tried to define what I mean by cheating in the paragraphs above. If you have any questions about whether a particular activity is permitted, please ask and I will clarify, usually to the whole class.
Let's assume you do understand what cheating is and are thinking about doing it. Why shouldn't you? Because habits die hard, and if you cheat once, it will become easier the next time, until it becomes a routine. Often students claim that they will stop when the pressure is less, for example, on the job. Sorry folks, but the pressures on employees in the "real world" can be even greater than those on students. Sometimes students excuse their cheating on the grounds that the assignment is "dumb". There are two things wrong with that argument: in the real world people set dumb requirements too and what you think is dumb may have a serious educational purpose.
Let's suppose you see someone else cheating. Should you turn them in? Think about it. Who is hurt by cheating? The students who did not cheat, because they have worked hard and actually learned something and the cheater got the same grade without learning. Even with absolute grading standards the cheater hurts you, because the value of your grade and degree is reduced by the cheating: employers recognize that the grades do not correspond to the knowledge. And the person who cheated could very well take your job or your slot in professional school on the basis of that grade. The cheater is often caught, but not always - and many continue and escalate their activities, ultimately causing a great deal of harm. That person could go on to cheat on a research project examining the safety and efficacy of a new drug, killing people as a result. Remember, if you see cheating, you may be the only person who can do anything to stop it, so don't be shy about telling your instructor. I can promise that I will keep any such reports confidential. Remember that your instructor will require more proof than your observations in order to justify punishment of the cheater, so don't expect instant response: students are innocent until proven guilty. I often give a warning if the evidence is weak and keep a close surveillance for more evidence.
4. APPEALS: Students who believe they have been graded unjustly may appeal; the following route is suggested:
Instructor
Department Chairperson
Dean of CSM
Provost and Vice-President for Academic Affairs
Vice-President for Student Life
Student Rights and Responsibilities Committee
President of TU
Last revision of lec331f01.htm August, 2001