CHEMISTRY 227 - ORGANIC CHEMISTRY I

Office Hours: MWF: 9:30 - 11:30 and TTh: 11 - noon, 2 - 4 PM and by appointment. I normally will be in my office during these hours, but I do have scheduled University commitments on some days. If you want to be sure I will be available, please call or e-mail to make an appointment. I am in my office or around the Department most days: feel free to make an appointment at a time convenient to you. You may also contact me by e-mail; many questions may be handled in that manner.

Course Description: Organic Chemistry I (CHEM 227) and II (CHEM 228) provide a two-semester sequence of courses designed to cover basic organic chemistry. These courses are intended to provide students a foundation in the fundamentals of the structure of organic compounds, their reactions, and underlying reaction mechanisms. Organic chemistry concepts provide the molecular basis for the basic concepts and observations of many other disciplines, including biology, biochemistry, chemical engineering, physiology, pharmacology, health sciences, and polymer science. Many of the new developments in these areas are based upon use of and knowledge of the molecular concepts.

Texts: John McMurry, Organic Chemistry, Fourth Edition, Brooks/Cole Publishing Company, 1996.

Susan McMurry, Study Guide and Solutions Manual for McMurry's Organic Chemistry, Fourth Edition, Brooks/Cole Publishing Company, 1996.

Molecular Models: Darling Models, Molecular Visions Molecular Model Kit, Texas A&M University Edition. Model Kits may be purchased from the TAMU Chemistry Club the first two weeks of the semester. A set of models should be considered as required in this section of organic chemistry. You will be using them during class and on examinations. I consider a set of molecular models to be as useful to you at some times during the course as the textbook. Any type of model set is okay, but the type sold by the undergraduate chemistry club (at below retail price) is recommended. You will also be using them during the organic lab (Chem 237) this semester.

Optional Software: Norbert J. Pienta, Organic Chemistry Toolbox, to accompany McMurry Organic Chemistry 4th Edition, Brooks/Cole Publishing Company, 1996. This Windows/MacOS software is available for use in the Learning Resources Center in the Sterling Evans Library and for purchase at the TAMU Bookstore. The software includes tutorials (on more than 450 screens) on the main topics of the course (structure, nomenclature, reactions, bio-organic, and spectroscopy), as well as the following visualization tools presented as stand-alone programs:

• molecular modeler (a screen version of plastic models)
• a Lewis Dot Structure drawing that can check formulas
• reaction animation
• a way to test knowledge of reactions
• spectral manipulation for infrared and 1H and 13C-NMR

To use the program, students first select a chapter and problem (problems are identical to how they appear in the textbook), followed by a menu of appropriate review topics and tools which will help them solve the problem. If students wish to see solutions, they can access them easily via a command on the menu. Answers can be saved in an electronic notebook or on paper. Alternatively, this program can be used as a reference or for review.

Free Structure-drawing Software: For those who would like to make use of software to draw chemical structures and reactions, two free software programs are available.

ISIS/Draw: Use this software for preparing written presentations or reports. You also can communicate chemical information by incorporating structures in MOL, TGF, and RXN formats in Internet mail messages as MIME attachments, provided the receiver of your mail also has ISIS/Draw. The URL for PC or Macintosh versions of this software is: http://www.mdli.com/prod/ioffer.html.

ACD/ChemSketch 3.5: Chemical drawing is fast and simple with a wide variety of atom and bond type buttons. Control font, valence, line thickness, arrows, color, placement, text annotations, etc. Import/Export includes a variety of formats such as MOL, ISIS Sketch, ChemDraw, and GIF. Cut and paste structures and reactions into a word processor. URL is: http://www.acdlabs.com/products/draw/chemsket.html

Internet Resources and Communications: There are WWW Homepages for this course and for the organic laboratory courses. Links to these courses, as well as to useful tutorials and animations of organic reactions, can be found on the TAMU Organic Chemistry Courses Homepage (URL = http://www.chem.tamu.edu/organic/orgmain.html). Links to copies of exams from this course from past semesters (from several instructors) will be posted on the Organic Homepage.

You are encouraged to investigate these materials either through computers at University Open Access locations (Open Access labs are located in the following buildings: Biochemistry & Biophysics, Computing Services Center, John R. Blocker, Read Building, West Campus, and Wisenbaker Engineering Research Center), through computer linked to ethernet from Dorms, or via modem from your off-campus home computer (Obtain information from Open Access locations for modem access to the University network.)

Internet access and some of the programs used in this course and the lab course are also available on six Organic Laboratory computers located in Room 2308. This room is open from 8AM - 5PM M-F. There is no printing available from these computers except through University Open Access computers if you know how to set that up. (There is no support available to provided assistance on this computers.)

Every student taking an organic laboratory course this semester will be required to have a University computer account, obtain an e-mail address, and communicate that address to the teaching assistant in your section. You are encouraged to use e-mail to handle questions that arise during this course and the laboratory course.

• Important announcements regarding this course will be posted in the Announcements Section on the World Wide Web Homepage for this course.
• Links to on-line copies of lecture notes and tutorials will be provided for every chapter.
• Answers to questions of general interest from the class submitted to me either in writing or by e-mail will be posted in the Questions sections of the course WWW pages.

Reserve Material: Examples of old exams will be available on the Web (through the course page and through the library on-line reserve pages at: http://er.tamu.edu/Science.html), but some may not cover exactly the same material to be covered on an exam. The answers are not provided on some of the exams. It will be especially good practice for you to work these exam problems, not to learn answers to questions, but how to answer exam-type questions. Use your learning groups to work these exams cooperatively and to discuss the reasons for the correct answers. I will be happy to answer any questions you may have concerning them, and will discuss questions from some of these old exams during a review session prior to the exam date. The general format of the exams, as well as the types of questions asked should be helpful to you.

Sources of Lecture 'Notes', Chapter Overviews, and Tutorials: The following are sources of study materials covering the topics covered in Chemistry 227.

On-line Sources -

• Organic Chemistry Lecture Slides: McMurry Chapters 1 - 11- by P. R. Young, Univ. of Illinois - Chicago (requires Javascript enabled and Chemscape Chime plug-in) (http://mephisto.chem.uic.edu/web1/LECTURE/232SYL.HTM)
• Organic Chemistry Online by P. R. Young from Univ. of Illinois at Chicago. Includes tutorials and interactive on-line quizzes. (requires Javascript enabled and Chemscape Chime plug-in)( http://homework.chem.uic.edu/)

Local Course Pack -

• Chem 227 - Sulikowski; Packet #260, Copy Corner ($12.10)

Course Structure: This section of Chemistry 227 will be structured as a problems-based, learner-centered Class. (See "Process-Centered Course Structure for Organic Chemistry" Handout for details) What Does This Mean? A learner-centered class will not look like your normal class - class periods will be just a series of lectures covering material covered in the text! Much class time will be spent learning to work problems - to prepare you to work the type of problems you find to be difficult on exams! For this to be effective, you must come to class prepared by studying the concepts and examples in the textbook before coming to class. The course will be structured to provide incentives for this preparation.

Class Periods: During class periods, I will discuss the most important sections of a reading assignment, but will not cover all of the assigned and/or important material in detail. Your primary source of factual information for this course should be the textbook, not lecture notes. During class periods, we will spend considerable time working problems and discussing the key concepts necessary to work these problems. These in-class activities will help prepare you for exams only if you have spent time reading the material in the chapter prior to class discussions. . Therefore, at or near the beginning of each class period, there will be a short Reading Quiz covering the key ideas and concepts from the assigned chapter! (See Reading Quizzes). These short Reading Questions will cover assigned material for that class period! (See Reading Questions). Class period(s) will include discussion of concepts and difficulties that have been requested by students prior to the class period. You will need to submit these questions by e-mail (preferred), note cards, or phone message prior to 9 PM the day before a class.

Supplementary materials may be presented in class at any time during the course. These materials are expected to help you understand important concepts and see the relationships of organic chemistry to other areas of interest to you. Questions relating to these materials may be found on exams.

Supplemental Instruction: The Center for Academic Enhancement is providing an advanced undergraduate student to coordinate peer-led review sessions during the semester. There will be three one-hour sessions each week at times that are suitable to the largest number of individuals. I urge you to take advantage of these review sessions. These sessions will provide opportunities for follow-up on in-class groups problems and practice your problem-solving skills. Studies (formal and informal) show that students who regularly attend SI sessions for chemistry courses have a significantly higher average grade in the courses than students who do not attend!

Review Sessions: Optional review sessions will be held most Sunday evenings at 8:00 PM in Rm 2102, Chemistry Building. These sessions will be devoted to learning problem-solving strategies, discussions of assigned problems, answering questions about material covered in lecture, discussion of sample exam questions, and demonstrations of useful software or WWW materials. No new material that would be considered 'required' will be presented in these sessions, but you should be attending unless you have no problem working the problems and understanding the concepts covered. Review sessions on the Sundays prior to the Tuesday exams are very important if you have questions about answers to practice exams.

Course Grade: Your grade in Chemistry 227 will be based on your performance on four 1-hour exams, 20 in-class reading questions (best 20 of 25 to 30 given), five group problem sets (best 5 of 6 or more given), and one 2-hour comprehensive final exam. Grades will be determined on the basis of 800 total possible points allocated as follows:

Grades will be based upon a percentage of the maximum total points earned by the student with the 2^nd highest total points (see discussion under exams) and not on the class median; therefore it would be conceivable (but not probable based upon past experience) that everyone in the class could make a B or better grade in the course. An estimation of grade cutoffs is A - 88; B - 77; C - 66; D - 55.

Reading Quizzes will be given at or near the beginning of every class period except for exam days. The questions for these quizzes will cover the concepts in the assigned chapter and their relationship to concepts covered previously. In some cases the questions may be similar to questions within the chapter. You should read the assigned material in the chapter and use the Summary at the end of the chapter to determine the key concepts to be studied and review/study those. You should also use the questions within the chapter and the Study Guide Outline at the end of the solutions for that chapter in the study guide to determine key concepts.

Problems worked in groups in class will not be graded unless they are assigned as one of the Group Problem Sets. However, participation will be noted, and points for a reading quiz will be recorded ONLY IF THERE HAS BEEN PARTICIPATION IN THE IN-CLASS PROBLEMS. Some in-class problem sets will be collected and graded on a S/U scale.

NO MAKE-UP QUIZZES WILL BE GIVEN since we are dropping a large number of these. Students failing to take at least 15 of the quizzes will receive grades of zero for the missing quizzes unless I have documented excuses for every quiz missed.

Exams will cover both the material in the text and the lecture (including any special interest topics introduced during a lecture for a chapter) as well as any other assigned material. The material in the course and, therefore, all exams are comprehensive, but material covered since the previous exam will be emphasized. Although some exam questions will be closely related to the assigned chapter problems, other types of problems will be covered also.

Although I have allowed students to use a Reminder with exams in the recent past, I have found that few students do a good job of preparation and use of this type of material. Therefore, no materials of this type can be used on exams.

Exam scores (mid-term and final) will be calibrated to the 98^th percentile score (2^nd highest score for this class) by the following formula: Recorded Exam Score = Raw score/2^nd highest score x 100. Thus every exam will have a high score of 100 (both highest score and 2^nd highest score will have scores of 100).

Make-Up Exams will be given only for documented excused absences as designated in the official Texas A&M University Student Rules. Section 7.5. If the student is seeking an excused absence (for assigned work or exams), the student must notify the instructor as soon as possible after the absence, but no later than the end of the second working day after the last date of absence. If the absence occurs the same day as a scheduled exam or other graded procedure, the student must notify his/her instructor or department by the end of the next working day after the absence in order to ensure full rights. If the absence was excused, the instructor must either provide the student an opportunity to make up the exam or other work missed or provide a satisfactory alternative completed within 30 calendar days from the last date of absence.

Documentation of such absences will be required for the absence to be considered excused. Exams missed for unexcused absences will be given a grade of zero. Make-Up Exams may differ significantly from the regularly scheduled exams give to the class and may include essay portions or other differences in question type.

Final Exam: A mandatory, comprehensive 200 point Final Exam will be given.

Exam Regrading: Occasionally an exam question is incorrectly scored. However, remember that the level of partial credit for any question is determined by me. If you question the grading of an exam question you must submit the entire exam to me for complete regrading. This is only fair. If you want credit for a question for which you were penalized, you must be willing to lose credit for a question for which you received extra points. The exam must be submitted for regrading within two class periods of the date the exam was returned to you. Do not write anything on the exam after it is returned to you if you wish to have it regraded. Attach a separate sheet indicating which question(s) you consider to be graded incorrectly. Exams upon which corrected answers have been marked will not be regraded. All exam scores will be considered final one week after the exam is returned to you.

Learning Groups: You will be assigned to a work group of 4 students for working the in-class and out-of-class group problem sets. Incentives for group study and peer-teaching include grading on scale based upon 2^nd highest exam rather than class median and Learning Group Bonuses on exams (see above). Learning groups are expected to notify me of non-performance of any member of the group.

Learning Group Bonuses: On any exam in which all members of a learning group (see below) earn a raw score of 80 or better, 10 points will be added to the total points of each member of the group (100 points maximum for any exam; 20 bonus points maximum per student for the course). If one member of a group misses an exam for an excused absence and the remaining members score above 80, the learning group bonus will be 5 points. Make-up exam scores cannot be used to qualify for these bonus points.

Group Participation Points: These points will be assigned at the end of the semester (prior to final exam) based upon each student's participation in learning as evaluated by the other members of a student's learning group. The maximum number of points is 10 points (equivalent to one group problem set).

Group Problems and Learning Groups: At least six group problem sets will be assigned and graded during the semester, some in-class and most out-of-class. For all out-of-class problem sets, you will be assigned to the same Learning Group, except that Learning Groups will be rearranged at mid-semester.. It is recommended that you consider making this group a regular study group. Exams are times in which you are asked to be the teacher - to give the explanations. This will be easier if you have practiced being a teacher in a learning group! Working cooperatively in a learning group can lead to bonus points on exams also (see above).

Cheating: Cheating will not be tolerated. The minimum penalty for cheating will be a zero score on the exam or quiz in question and an entry into your record in the Department of Student Life. Please read the appropriate section of the Texas A&M University Regulations on this subject.

Study Tips: Although there is a lot of 'content' in this course, the most important 'skill' that you must develop to do well in this course is problem-solving skills. Your mathematical prowess will be little used; we do not solve numerical problems to any extent. You will need skills of observation, classification, and logical reasoning. A few of you already have those skills; most of you are going to need to work significantly harder in this course because you will have to both learn content and problem-solving. You cannot learn problem-solving by reading/memorizing the book or learning/memorizing the answers to problems in the book. You must spend significant amounts of time practicing problem-solving. The important thing to learn is not 'the answer' to a problem, but 'what did I have to do' to generate the answer. It has been pointed out that if you know the answer to a question, or know exactly what to do to get the answer, the question is not a problem, it is an exercise. Our exams will have few questions that are exercises; most will be problems. To quote Prof. George Bodner, "Problem-solving is what you do when you do not know what to do". You cannot expect that the 'answer' to a 'problem' on an exam will just pop into your head; you will need to go through several steps to 'generate' a logical answer.

Learning organic chemistry has similarities to learning a language. Many of the words we use will be in English, but will define concepts you have never used before. Many reactions are like a sentence: subject (reactant) plus a verb (reagent) results in an object (product) where there are 'rules' that allow only certain sentences to be valid. However, in addition to English words (e.g. diastereoisomers) you will encounter a very structured symbolic language (see a few of the different symbolic representations for a single molecule below) that will look like hieroglyphics unless you 'learn the language'.

You cannot expect to be able to do logic problems unless you understand the language. Individuals who do not become proficient in the 'language' of organic structures have a miserable time in organic classes.

Here are some other tips:

Read the "study guide' found at the end of each chapter in the Study Guide (e.g. p. 13 for Chapter 1) and the Summary and Key Words boxes at the end of each chapter before reading the text. This notifies you of what the key concepts, etc. are most important.

Work the assigned problems within the chapter as you come to them. This will help make sure you are getting the key concepts. Again, the important feature is not the answer, but what concept, generalization, or rule was used to determine the answer.

Don't just rationalize the answer in the answer book. Write down the concepts and approach used to solve the problem. Where in the book do you need to go if you can't remember what you need to know? Learn to classify the problems based upon what is needed to solve them.

Don't play 'catch-up'. Read ahead of the lecture. Listen in class; ask questions. Go to SI sessions and review sessions. NEVER GET BEHIND; NEVER GET BEHIND; NEVER GET BEHIND!

Practice the 'language'. Write down answers to problems; practice writing the hieroglyphics. You are going to have to do this on exams. You will make too many 'spelling errors' or 'write too slow' even when you 'know the answer' unless you practice to develop your proficiency in writing representations for structures and reactions.

Remember that on exams, you are the teacher. You must respond to questions and give a logical answer. We may not always ask you to explain you answer, but unless you know enough to explain your way to the answer, you are unlikely to have generated a correct answer. You must practice this skill before the exam unless you want to try learning during the exam. You can develop this skill by self-examination, but you also may want to practice it with study partners. As you encounter new concepts, try to imagine giving a short lesson (in your own words, not memorizing the text) to another beginning student. Again, this could be done in group study.

If you study in a group, make sure you are learning to solve the problems independently, not just observing others solve the problems. Be sure you are giving each problem an honest independent effort before using the group to obtain help over a stumbling point. Use others to test your grasp of concepts and ability to explain (teach).

Likewise, do not go to the answer book too quickly. Try to find the information needed in the book. If you have to ask someone for help or look at the answer make sure you make note of (and learn) what you had missed. If it was important to solve that problem, it very well may be important in solving a problem on an exam.

One hallmark of good learners is their recognition that everything is connected. What you learn in one place can help you understand something else. This is very true in organic chemistry. When faced with new and unfamiliar information, look for connections to things you already know. This will make it more useful to you and easier to remember. A stack of unconnected facts is very unstable; unless you make connections your stack is likely to collapse totally about two-thirds of the way through the semester!

Organic chemistry is elaborative. We will teach you some basic concepts at the beginning, but much will be left out until later. We will add to (elaborate) these concepts as we go through the course. You need to review and remake some connections. Think of making a large painting. You start with a sketch that gets filled in, sometimes with erasure and correction, over a period of time. If you concentrate too much on the details of one corner, it may have no meaning unless you draw back to 'see the whole picture.

Use self-constructed assessments. One way to test your own proficiency is to create your own problems. For example, take any subject heading in the course ("resonance forms", Lewis acid-base complexes", etc.) and write it on a blank sheet of paper. Then create - not look up or recall from memory - ten to fifteen examples based on the general principles covered for that topic. You will encounter 'examples' that will raise questions about the limits or generality of the principles. These are good questions for review sessions or a class period where the topic is being discussed.

Use old exams to assess your mastery of material and learn where you need additional study. Exams from other instructors may differ in the specific types of questions, but they are testing knowledge of the same material. Remember, you can't just look at the questions and say, "Yes, I know the answer to this one". What you need to know is 'how do you work this type of problem?'. Check for correctness with another student in your study group; with your SI instructor, or with me.

Course Syllabus: Approximate Schedule

Exam Schedule:

Tentative Dates of Exams

Exam 1 - Tues., Sept. 22

Exam 2 - Tues., Oct. 13

Exam 3 - Tues., Nov. 3

Exam 4 - Tues., Nov. 24

Final Exam Section 508 - Friday, December 11, 1998, 12:30 - 2:30 pm