Week	Topic	McM	Enrichment & Summaries	SG
Jan 27	Conjugated Double Bonds	14	Nomenclature, Insect Control, Terpenes, Rxs	IV
Feb 3	Aromatic Compounds	15	Aromatic Theory, NMR Evidence for Aromaticity, Determining and writing mechanisms	VII
Feb 14	Substitution of Aromatics	16, 17.3, 17.10-17.11	Rxs & Syn; Effect of Substituents	VII
Feb 17	Carbonyl Compounds: Aldehydes and Ketones, Carbohydrates EXAM 1, McM 14 - 17; see S02 Exam 1	19 (not 19.14), part of 25	Nomenclature, Redox Reactions and Reducing Agents, Rxs, esp with nucleophiles, and Syn	IX
Feb 24	Carbonyl Compounds: Carboxylic Acids	20	Nomenclature, Acids, NSAIDS, Oxidizing Agents, Rxs & Syn	VIII
Mar 3	Carbonyl Compounds: Acid Derivatives: Halides, Esters, Amides	21	Nomenclature, Chloride Rxs & Syn, Ester Rxs & Syn, Amide Rxs & Syn	VIII
Mar 10	Acid Derivatives: Halides, Esters, Amides	21, parts of 27, 31	Lipids, Condensation Polymers	VIII
Mar 17	Carbonyl Compounds: Reactions at the a-Carbon: Enols and Enolates EXAM 2: McM 19-21, parts of 25, 27, 31; see S02 Exam 2 and Exam 3	22	Reactions & Synthesis with Enolates	X
Mar 24	Spring Break
Mar 31	Carbonyl Compounds: Reactions at the a-Carbon	23	Rxs and Synthesis with Enolates	X
Apr 7	Carbonyl Compounds: More Reactions at the a-Carbon	23, 19.14	Synthesis with Enolates; Nucleophiles & Reducing Agents	X
Apr 14	Amines EXAM 3: McM 22 - 23; see S02 Exam 4	24	Acids and Bases, Reactions & Synthesis	XI
Apr 21	Complex Amines, Neurotransmitters, Drugs that Affect the Brain, Amino Acids, DNA	parts of 26, 28	Neurotransmitters	XI
Apr 28	Carbohydrates	25		XII
May 5	Review Using Complex Synthesis	20	Tetracycline	I-XI
May 17	Final Exam	all	10:15 am, Friday May 17!!!	I-XI

NOTE that Chapters 12, 13 and part of 14 will be discussed in the laboratory; most of the test questions on these topics will also occur in the laboratory.

INDEX TO THIS SYLLABUS

1. Required Purchases

2. Some Secrets to Success

3. Problem Sessions

4. Grading and Examinations

5. Laboratory

6. Sources of Help

7. Ethics for Students in Organic Chemistry

1. Required Purchases

1. Required:
   1. Organic Chemistry, John McMurry, 5th edition, Brooks/Cole division of Thomson Learning, Apcific Grove, CA, 2000.

   2. Supplementary Enrichment Materials Required for Organic Chemistry I, L. M. Sweeting, 1998 (downloadable from the WWW). Selected materials are listed and linked under Enrichment and Summaries above.

2. Recommended:
   1. Study Guide and Solutions Manual for McMurry 's Organic Chemistry, Susan McMurry, Brooks/Cole (ITP), Pacific Grove, CA, 2000. 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 II, L. M. Sweeting, 1998 (WWW)

   4. Graphical Reaction Summaries available free from my WWW site via http://www.towson.edu/~sweeting/orgrxs/reactsum.htm along with other WWW resources on nomenclature and reactions linked to these pages. Use these on-line as a review. They are especially useful in the quiz versions.

   5. Learning Objectives and Study Guide by L. M. Sweeting, referred to above as LOSG and available free on the WWW via http://www.towson.edu/~sweeting/studguid.htm. You may download it, but please do not use the Chemistry tutoring or learning center or other campus facilities for printing (we are trying to save money and trees).

   6. Molecular Models (a,b,c,d usually available at TU) - these are less needed in 332 than 331. The disk that comes with McMurry provides some 3-D examples, but thus far they are not mobile and thus not as convincing.
      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.

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   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.

   In 331, the course concentrated on language and structure, followed by some classes of chemical reactions. In 332, the focus is on reactions (their products and mechanisms) and applications. To learn the reagents and products, 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. 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. Read the chapters ahead of time: you won't understand everything, but you will learn much more in the lecture classes. Topics emphasized in class (relative to the book) will be those which merit extra time because of difficulty or importance. I will be providing a variety of enrichment materials during the semester to assist you in your learning and help relate organic compounds to your other courses and interests.

   I strongly recommend that you make reaction summaries, either on flash cards or on sheets of paper, as an aid to learning reactions. Your summary might be graphical or in the form of a list (see the WWW graphical reaction summaries for one way); if you have ever made a concept map, you can use the method you used there. 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 some problems in the LMS 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 on time, you do some of each kind. In addition, the WWW site has two sets of drill problems in the Reaction Summaries and Quizzes to remind you of the reactions for each functional group.

   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. Your Study Guide & Solutions Manual also has practice exams. Exams from previous years will be placed in the library copy center for your use; you must purchase the complete set. 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.

   3. Problem Sessions

   In the Fall of 1990, I tried a change in classroom style. I set aside one class per week for questions and problem-solving (by students in groups, with my help). This session was very popular with the students, who were more than willing to do the extra work to make it possible. 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. l usually lecture Monday and Wednesday and have problem sessions Friday, 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.

   4. Grading and Examinations

   There will be three exams (rarely four) during the term plus a cumulative final. 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 Study Guide is more complete; things that are in there but not in your text or my lectures will not be on the exams. 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)

   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%, lecture tests 35%, 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 with this lecture syllabus. 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 (not just reading) - bring your notebook, goggles and text each time and plan what you are going to do. Poor preparation is dangerous to your health and everyone else's.

   6. Sources of Help

   1. Text (F&F) and the Solutions Manual or Study Guide and Additional Drill Problems. Don't look up the answers until you have tried the problems (not just looked at them), and never just look up the answers - examine and try to understand the reasoning.

   2. WWW Reaction Summaries and Quizzes, Nomenclature, Mechanism, etc. provided in the course web site or with links therefrom. You may use the computers in the Chemistry Learning Center when it is open.

   3. Instructor. By appointment or during office hours; if you stop by without an appointment I may be able to help then, but I may have other duties that prevent me from doing so. By phone or e-mail, but don't expect to reach me quickly this way, since I only check my mail about once per day or two.

   4. Tutor, Liina Ladon and assistants (Smith 538). Software available in the tutoring center, especially Orgtutor and RxDriller.

   5. Learning Objectives and Study Guide by Sweeting (known here as LMS Study Guide or SG), and other organic texts (available in the library, tutoring center, etc.) The LMS Study Guide is organized by functional group and contains specific references to several texts for each topic (it was designed to be partly independent of textbook).

   6. Internet. Don't be shy about checking around to see who else has put organic chemistry course information on the Web; the Chemistry tutoring center has some additional sites identified (e.g. http://www.anachem.umu.se) and new ones are being created every day. Let me know if you find any that are particularly helpful.

   7. 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

   8. Old exams which are available in the library copy center (Copies+) for the cost of duplicating. Please note that the content of exams varies somewhat from year to year with textbook and course pacing. Look at the content to determine the extent of relevance.

   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 (tests dates and content are announced in class).

   2. ATTENDANCE is required for all tests and laboratory periods (lecture and activity). Any student arriving late for laboratory lecture may be denied permission to work in the lab for safety reasons.

   3. 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 will never be allowed the opportunity again in this course.

   4. 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 with single authors will be considered plagiarized and will be given no credit. If you worked with others, give them credit.
      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. 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? 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, because 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. 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. I usually give a warning if the evidence is weak and keep a close surveillance for more evidence.

      APPEALS: Students who believe they have been graded unjustly may appeal; the following route is suggested:

      • Instructor

      • Department Chairperson

      • Dean of CSM

      • Provost

      • Dean of Students

      • Student Rights and Responsibilities Committee

      • President of TSU

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