Chemistry 21 Organic Chemistry I

Transcription

1 Chemistry 21 Organic Chemistry I Fall, 2016 Dr. J. F. Harwig Office: SCI 274 Office Hours: T,Th 10:30-12:30 Voice Mail: Harwig_John@smc.edu Homepage: PREREQUISITES Chemistry 11 and Chemistry 12 with minimum grades of C OBJECTIVES Chemistry 21, first semester organic chemistry, is a rigorous systematic introduction to the chemistry of carbon compounds. The course provides a foundation for further work in organic chemistry (Chemistry 22/24) and biochemistry (Chemistry 31). Chemistry 21 encompasses both modern organic chemical theory and the descriptive chemistry of the principal functional groups. Topics include bonding and structure, nomenclature, stereochemistry, structure-reactivity relationships, and synthesis and reactions of the hydrocarbons and derivatives. Emphasis is placed on application and interpretation of experimental data in determination of molecular structure and in elucidation of reaction mechanisms, and on development of practical strategies for synthetic inter-conversion among functional groups. The laboratory work focuses on techniques of synthesis, isolation, purification and analysis, both in theory and in practice. 1) Textbook: David Klein, Organic Chemistry, 2nd Edition. MATERIALS and RESOURCES 2) Study Guide/Solutions Manual: David Klein, Study Guide & Solutions Manual to accompany Organic Chemistry, 2nd Edition. 3) Organic Molecular Model Kit. 4) Lab Techniques Manual: Mohrig, Alberg, Hormeister, Schatz and Hammond, Techniques in Organic Chemistry, 4th Edition. 5) Laboratory Notebook: 101/4 x 77/8 inches, 5 mm x 5 mm quad ruled, permanent binding. 6) Laboratory Locker Fee Card. 7) Scientific Calculator. 8) Chemistry template. 9) Personal Protective Equipment (PPE): a) Chemical safety goggles. b) Nitrile gloves. c) Flame-resistant (blue) knee-length laboratory coat.

2 Quizzes There will be a short (~ 20 minute ) quiz most Thursdays, except for weeks in which an exam is scheduled, for a total of 7 quizzes. No make-ups will be permitted. One quiz score will be dropped at the end of the semester. If a quiz is missed, for any reason, that quiz will be the one dropped. If all quizzes are taken, the lowest score will be dropped. The quizzes will cover the material under study at the time. Specific topics will be announced in advance. Exams There will be 4 exams. The exams will cover the textbook, the lectures, and the laboratory sessions. No make-ups will be permitted. One exam score will be dropped at the end of the semester. If an exam is missed, for any reason, that exam will be the one dropped. If all exams are taken, the lowest score will be dropped. Exam No. Week Date Text Chapters 1 5 Thu 9/29 1, 2, 3, Thu 10/27 5, 6, Thu 11/17 8, 15, Thu 12/8 9, 10, 11 Homework Organic chemistry is not a spectator sport. You cannot learn organic chemistry by passively reading the textbook and listening to the instructor. You learn organic chemistry by becoming actively involved in it and doing it. One of the most important aspects of active participation in the learning process is problem solving. For each chapter of the text there are assigned problems. You should, at a minimum, work these problems. Complete worked-out solutions are provided in the Study Guide & Solutions Manual. Do not merely look at these solutions; make a serious effort to work the problems on your own. The solutions should only be used to check yourself after you have finished a problem or to seek help in getting started if you become totally frustrated with a problem. Homework will not be collected or graded. However, the level of learning and corresponding success in the course are related to the time and effort spent in problem solving. Laboratory Experiments Laboratory experience is one of the most important aspects of an organic chemistry course. Almost all aspects of organic laboratory work, from experimental theory and techniques to notebook keeping and report writing, are new to most students and different from most laboratory experience in general chemistry. A total of 8 experiments will be performed. Make-ups will not be possible. One lab score will be dropped at the end of the semester. If a lab is missed, for any reason, that lab will be the one dropped. If all labs are completed, the lowest score will be dropped. Full details of the laboratory work will be presented in separate handouts distributed at the laboratory orientation session. Final Exam (comprehensive and mandatory) - Thursday, December 15, 8:00-11:00, SCI 157

3 * Summary * 3of points = 300 points 6 of 7 20 points = 120 points 7 of 8 lab 15 points = 105 points final 150 points = 150 points Total = 675 points * Grading Scale Table * Percent of Course Grade Point Range Total Points Possible A B C D F < 337 < 50 The table above shows the minimum guaranteed grade ranges. At the end of the course some slight downward curving of these ranges is possible, if appropriate - - but don't count on it. ADDITIONAL COURSE REQUIREMENTS Attendance Successful completion of this course requires full participation in all class activities, including lecture sessions and laboratory periods. Regular attendance in lecture and laboratory is both expected and required. Excessive absences may result in being dropped from the course. Punctuality is also important - plan to arrive in class on time. Remember to allow for parking problems, etc. Students who arrive late not only miss important material, but also disrupt the class. Withdrawal Be aware of college regulations and deadlines regarding dropping classes: Check your Corsair Connect account to find drop dates for enrollment fee and tuition refunds, to avoid a W on your permanent record, or to receive a guaranteed W.. If you want to drop the course, it is your responsibility to drop yourself online, otherwise you could inadvertently end up with an F on your transcript. Code of Academic Conduct The Academic Honor Code of Santa Monica College will be strictly enforced in this course, and academic dishonesty in any form will not be tolerated. This includes, but is not limited to, cheating on exams, changing answers on graded assignments, copying of lab reports, and falsification of lab data.

4 SOME ADVICE ON SUCCESS IN THIS COURSE 1,2 Organic chemistry opens a whole new world of chemical knowledge and represents a new way of thinking about chemistry. The study of organic chemistry involves not only learning a seemingly endless amount of information, but also processing that information in an efficient manner. Most beginning students find organic chemistry to be challenging, and many find it to be quite difficult, at least initially. Even students who have done well in general chemistry, where the approach is largely mathematical, sometimes find themselves struggling in organic chemistry, where the approach in primarily conceptual. Organic chemistry is a highly organized and very precise discipline. It involves sorting facts, analyzing problems, looking for patterns and reasoning by analogy. Learning organic chemistry is like learning a new language. The key to success in organic chemistry is not much different from any other chemistry course: active participation in the learning process, consistent daily effort, keeping up rather than catching up, and maintaining a positive attitude. Success involves hard work, for which there are no shortcuts. Organic chemistry is an intense and demanding 5 unit course for which you will spend 9 hours per week in class. You should expect to spend at least hours per week on your own time outside of class if you want to complete the course successfully, with a good grade and a strong base of knowledge and skills needed for continuing in chemistry or other science courses. The most important advice to remember (and follow) in studying organic chemistry is DO NOT FALL BEHIND! The individual steps to learning organic chemistry are quite simple; each by itself is relatively easy to master - but they are numerous, and the subject can quickly become overwhelming if you do not keep up. Before many of the theories and mechanisms were figured out, organic chemistry was a discipline that could be mastered only through memorization. Fortunately, that is no longer true. You will find many unifying ideas that allow you to use what you have learned in one situation to predict what will happen in other situations. So, as you read the book and study your notes, always making sure that you understand why each chemical event or behavior happens. When the reasons behind reactivity are understood, most reactions can be predicted. Approaching the course with the misconception that to succeed you must memorize hundreds of unrelated reactions could be your downfall. There is simply too much material to memorize. Understanding and reasoning, not memorization, provide the necessary foundation on which to lay subsequent learning. Nevertheless, from time to time some memorization will be required: some fundamental rules will have to be memorized, and you will need to learn the common names of a number of organic compounds. The scientific discipline of organic chemistry is NOT merely a compilation of principles, but rather, it is a disciplined method of thought and analysis. Students must certainly understand the concepts and principles, but more importantly, students must learn to think like organic chemists... that is, they must learn to become proficient at approaching new situations methodically, based on a repertoire of skills. That is the true essence of organic chemistry. Students who study organic chemistry to gain entrance into medical school sometimes wonder why medical schools pay so much attention to this topic. The importance of organic chemistry is not in the subject matter alone. Mastering organic chemistry requires a thorough understanding of certain fundamental principles and the ability to use those fundamentals to analyze, classify, and predict. The study of medicine makes similar demands: a physician uses an understanding of certain fundamental principles to analyze, classify, and diagnose. Read the appropriate sections of each chapter before you come to the lecture on those sections. Take good comprehensive notes during lecture. Then, as soon as possible after each lecture, re-read the same sections in the text, along with the notes you took. Have pencil in hand to work on the problems relating to those topics. As you go along, make a list of your questions to bring to class or to submit on ecompanion. 1 Taken in part from Klein, Organic Chemistry, 2nd Edition. 2 Taken in part from Bruice, Organic Chemistry, 7th Edition.

5 LECTURE SCHEDULE Week Dates Topics Quiz / Exam (Thursday) 1 8/30, 9/1 Course Introduction, Perspective and Scope Ch. 1 A Review of General Chemistry: Electrons, Bonds, And Molecular Properties /6, 9/8 Ch. 1 (Continued) Ch. 2 Molecular Representations Quiz 1 3 9/13, 9/15 Ch. 2 (Continued) Quiz 2 4 9/20, 9/22 Ch. 3 Acids and Bases Ch. 4 Alkanes and Cycloalkanes Quiz 3 5 9/27, 9/29 Ch. 4 (Continued) Exam /4, 10/6 Ch. 5 Stereoisomerism /11, 10/13 Ch. 5 (Continued) Ch. 6 Chemical Reactivity and Mechanisms Quiz /18, 10/20 Ch. 7 Substitution Reactions Quiz /25, 10/27 Ch. 7 (Continued) Exam /1, 11/3 Ch. 8 Alkenes: Structure and Preparation via Elimination Reactons /8, 11/10 Ch. 8 (Continued) Quiz /15, 11/17 Ch. 9 Addition Reactions of Alkenes Exam /22 [Tuesday] Ch. 9 (Continued) /29, 12/1 Ch. 9 (Continued) Ch. 10 Alkynes Quiz /6, 12/8 Ch. 10 (Continued) Exam 4 Thu 12/15 Final Exam 8:00-11:00

6 LABORATORY SCHEDULE Dates 1398 (M) / 1399 (W) Week 1 M 8/29 / W 8/31 Week 2 Week 3 M 9/12 / W 9/14 Week 4 M 9/19 / W 9/21 Week 5 M 9/26 / W 9/28 Week 6 M 10/3 / W 10/5 Week 7 M 10/10 / W 10/12 Week 8 M 10/17 / W 10/19 Week 9 M 10/24 / W 10/26 Week 10 M 10/31 / W 11/2 Week 11 M 11/7 / W 11/9 Week 12 M 11/14 / W 11/16 Week 13 M 11/21 / W 11/23 Week 14 M 11/28 / W 11/30 Week 15 M 12/5 / W 12/7 Laboratory Activity Laboratory Introduction, Overview and Safety Discussion of Lab Notebooks and Lab Reports Locker Check-In Lab 1: Synthesis of Salicylic Acid No Lab Completion of Lab 1: Melting point / C-13 NMR analysis of product Lab 2: Synthesis of Ethanol by Fermentation of Sucrose Begin: Preparation of fermentation mixture Completion of Lab 2: Distillation and analysis of product Lab 3: Separation of Excedrin Components I. Extraction Lab 4: Separation of Excedrin Components II. Column Chromatography Completion of Labs 3 and 4 Lab 5: Isolation of (R)-(+)-Limonene from Orange Peels Lecture: Ch. 15 Infrared Spectroscopy and Mass Spectrometry Lecture: Ch. 16 Nuclear Magnetic Resonance Spectroscopy Lab 6: Spectroscopy - Mass Spec / IR / NMR Lecture: Ch. 11 Radical Reactions Lab 7: Phase Transfer Catalysis: Synthesis of Butyl Benzoate Lab 8: Stereochemistry of Bromine Addition to Trans-Cinnamic Acid Locker Check-Out

7 CHEM 21 STUDENT LEARNING OUTCOMES (SLOs) 1. The student will follow a logical process based on well-established scientific principles and demonstrate the ability to use the appropriate problem-solving techniques to solve a scientific problem such as an organic synthesis comprised of two or more steps, or a determination of the structure of a compound based on spectroscopy (IR, NMR, MS) and/or chemical evidence. 2. When conducting a laboratory experiment, the student will follow written procedures commonly used in the organic lab (such as reflux, distillation, extraction, recrystallization, and melting point determination) accurately and safely. When completing a lab report, the student will apply the scientific method correctly by being able to state a hypothesis, take careful measurements, estimate uncertainties and draw appropriate conclusions based on gathered data and scientific principles. 3. The student will explain observable phenomena using appropriate scientific theories, such as writing a reaction mechanism consistent with observed facts or utilizing appropriate structures to represent different types of organic molecules and species.