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Unformatted text preview: Organic Chemistry: CHEM 151L.001: Fall 2007 Instructor: Holly L. Sebahar, Ph.D. Office: French Family Science Center (FFSC) 1225 Phone 660-1615; e-mail address: [email protected] Office hours: Wednesday and Thursday 2-3:30 pm or by appointment. Suggested Course Materials: 1. Loudon, G.M. Organic Chemistry, 4th ed.; Oxford University Press: New York, 2002. 2. Loudon, G.M., Stowell, J.G. Study Guide and Solutions Manual to accompany Organic Chemistry, 4th ed.; Oxford University Press: New York, 2002. 3. Molecular Modeling set - you can pick one up on your own or buy one for $25 Wed. 8/29 before class (LSRC) or 30 minutes before lab 9/3-9/14 (FFSC). 4. Goggles for sale at the bookstore or in FFSC ($5) thirty minutes before lab 9/3-9/14. Class Meeting: Lecture: M, W, F 10:20 am -11:10 am. Room: LSRC B101 (Love Auditorium). Day M W F M W F M W F M W F M W F M W F M W F M W F M W F Date 8/27 8/29 8/31 9/3 9/5 9/7 9/10 9/12 9/14 9/17 9/19 9/21 9/24 9/26 9/28 10/1 10/3 10/5 10/8 10/10 10/12 10/15 10/17 10/19 10/22 10/24 10/26 Topic Syllabus and Alkanes review basics Alkanes constitutional isomers Alkanes conformational isomers Cyclohexane Cycloalkanes conformational analysis Finish cycloalkanes, polycyclic compounds Introduction to mechanisms Acid/base chemistry Alkenes - Nomenclature, structure, properties Alkenes Relative stabilities, Addition of HX Alkenes Hammond's Postulate Alkenes Reactions Alkenes Reactions Finish Alkenes, Intro synthesis in o-chem EXAM I Stereochemistry - definitions Stereochemistry Stereochemistry NO CLASS HAPPY FALL BREAK Stereochemistry of Reactions Stereochemistry of Reactions Finish stereochem. of rxns, Intro ROH, ROR Acid/base properties of ROH, RMgBr, RLi Substitution and Elimination SN2 E2 SN1 and E1, carbenes Reactions of ROH, RSH Chapter 1-2.2 (review chapter 1 on your own) 2.4,- 2.6 (2.8, 2.9 on your own; 2.7 later) 2.3 (bring ethane & butane to class) 7.1-7.2 (bring cyclohexane to class) 7.3, 7.4a,b (cyclohex. & 2 Me groups) 7.5, 7.6a,b 3.1-3.3 3.4-3.6 4.1-4.4 4.5-4.7 4.8 4.9, 5.3 (5.2 on your own) 5.1, 5.4 5.5 (5.6-5.7 on your own), 10.11 6.1 (bring your models!) 6.2-6.5 6.6-6.11 (6.12 on your own) 7.4c (skip 7.4d), 7.7-7.8 7.9 7.9 continued, 8.1-8.5 8.6-8.8 9.1-9.4 9.5 9.6 9.8, 11.6b 10.1-10.4 M W F M W F M W F M W F M W F M W F Th 10/29 10/31 11/2 11/5 11/7 11/9 11/12 11/14 11/16 11/19 11/21 11/23 11/26 11/28 11/30 12/3 12/5 12/7 Reactions of ROH, RSH continued Finish Chapter 10 Exam II Synthesis of Epoxides and Ethers Reactions of Epoxides and Ethers Synthesis and Reactions of Glycols 10.5-10.8 (10.9 on your own) 11.1-11.2 11.3-11.4 11.5 (11.6-11.9 on your own) Strategies for Synthesis / Structure Elucidation 2.7, 4.3 IR 12.1-12.5 Mass Spectrometry 12.6 NMR intro to theory 13.1-13.2 NO CLASS HAPPY THANKSGIVING BREAK NO CLASS HAPPY THANKSGIVING BREAK NMR NMR NMR
13 13.3 13.4 (13.5 briefly) C NMR Exam III Review 13.6-13.10 12/13 (2-5 pm) FINAL EXAM Cumulative NOTICE: This schedule is subject to change. Together we will finalize the schedule at our first meeting. Grading: 3 50-minute exams @ 150 points Laboratory (normalized) Final Examination Total Points = 450 points = 250 points = 300 points =1000 points The median point total for the class has been traditionally set at approximately a B-. Exams: The focus of each exam will be on the chapters recently covered in the lecture and associated homework and recitation problems. However, realize that we will continually be building on the fundamentals so you will be responsible for all material covered prior to the exam. Use of molecular models is permitted (and encouraged!) during exams, but they may not be shared. Academic Honesty: All students are expected to abide by the Duke Community Standard. Any and all cases of suspected academic dishonesty will be turned over to the judicial board. A discussion on the Duke Community Standard can be found at http://www.integrity.duke.edu/ugrad/student.html. I take this very seriously. Please let me know if you have any questions about what is acceptable. Absences: If an exam is missed because of a short-term illness, a student may submit an excuse on-line at the web address http://www.aas.duke.edu/trinity/t-reqs/illness/. This url is also posted on Blackboard under External Links. If an hour exam is missed for another legitimate reason, planned or unplanned, then a Dean's excuse is required. NO MAKEUP will be given FOR EXCUSED or UNEXCUSED EXAMS. If the exam is excused the 75% lecture portion of the final class grade will be determined from the exams that were taken. An unexcused absence from an exam will result in a score of zero. Re-grades: It is to your advantage to compare your exam to the key to make sure you understand your mistakes and also to check for grading errors. If you notice a grading or addition error the exam may be submitted for re-grading. Please fill out completely the re-grade submission form available on Blackboard under Course Documents. In the case of student-perceived grading errors or point assignment, the entire exam will be re-graded, not just the problem in question. Re-grades will be accepted up to one week following exam distribution. Return exam with attached re-grade submission form to Dr. Sebahar in Room 1225 FFSC. DO NOT CHANGE YOUR EXAM IN ANY WAY. Prior to return of exams, a considerable number of the exams, perhaps all, will be photocopied. Individuals who make submissions for re-grades that raise suspicions will have the copy of the original exam and the exam submitted for re-grading compared. Discrepancies between the two will constitute academic dishonesty and will be dealt with appropriately. Recitation: Recitation Worksheets will be posted in the Recitation Section of the Course Blackboard site. The questions have been chosen because they reflect the type of problems you will see on the exams. During the recitation meeting the instructor will focus on covering the problem solving techniques required for the present material. The goal will not be to cover the entire worksheet but to go over the skills and techniques required to solve all of the problems. The answer keys will be posted on Tuesday evenings. I welcome feedback about recitation throughout the semester. Recitation instructor: Marc Adler ([email protected]) Note: Recitation will begin the second week of class: September 3-7. Laboratory: Enrollment and attendance in CHEM 151 laboratory is required for every student enrolled in CHEM 151L. If you have completed the lab a previous semester and plan to use your score please talk to me ASAP. Note: there is not a separate laboratory manual - lab experiments, etc are available on the Blackboard site (2007 Fall) Chem 151 Laboratory (11L-72L) under Course Documents. To compensate for variations in grading by different teaching assistants, lab grades will be normalized at the end of the term so that the average for each TA is the same. Laboratory Director: Holly Sebahar. NOTE: The first week of lab will be Monday, September 3 Friday, September 7. Hints on Succeeding in Chem 151: 1. Examine how you did in General Chemistry. If you were happy with the amount of material you learned and your grade keep it up! If you were not satisfied then something has to change if there is any hope of doing better in organic chemistry. 2. Do not get behind. We will be covering a large amount of complicated material in a short amount of time and each concept will build upon the knowledge you have already accumulated. For these reasons I encourage you to stay caught up and spend time daily reading the text, solving problems, and/or practicing mechanisms and synthesis. Do NOT try to CRAM or MEMORIZE. Regular, rigorous training for the brain is necessary to compete in this o-chem marathon! 3. Prepare for lecture. Spend at least a few minutes before each lecture to scan through the topics to be covered that day. Lecture will focus on the most challenging concepts from the text and the application of these concepts. Lecture will seem more relevant and interesting if you have a basic familiarity with the assigned material before you walk into class. After lecture you can then go back to read more carefully the sections that you found most problematic. Note: you are responsible for material in the assigned chapters unless I specifically announce otherwise. It is not fair to assume that because something was not presented in lecture that it will not appear on an exam. 4. Practice. On the exam you will be asked to solve problems. Therefore, it is highly recommended that you do all of the assigned problems from the chapters and the recitation worksheets early and until you have mastered the problem on your own. Make sure you pay attention to the concepts covered in each problem and not just on getting the correct answer since you will not see the same problem on the exam, but one that is related. It may also be helpful to do the problems embedded in the text to get a feel for how well you grasp each section. If you find you have difficulty go back and read that section more carefully. Other organic texts can be found in the BES library and each contains problems that may be helpful if additional practice is necessary (McMurry is a good one). The worst thing you can do for yourself is to do the problems with the solutions guide open next to you. If the following sounds familiar, STOP! "While working through problem 999 I was stuck. I glanced quickly at the answer key and suddenly the problem seemed straightforward and easy so I moved on the next problem." During the exam you are ON YOUR OWN... it is to your advantage to struggle through the problems on your own as much as you can before consulting the solutions guide. If you must consult the answer for guidance this means that some time before the exam will have to come back to this problem again (and again until you can finish it on your own.). 5. Learn from your mistakes: A key will be posted shortly after an exam has been graded. Make sure you understand where you made your mistakes and how to correct them. Remember, everything in O-Chem builds upon the basics chances are, if something was important enough to show up on a mid-term exam it will show up again in a slightly different form on a later exam and in 152. 6. Be realistic about your exam readiness. Sometime before the exam put yourself in a true test taking situation. You could do one of the old exams (without the answer key handy) or put together a practice test of your own by working through the homework and recitation problems in a random order. Either way, the key is to do the problems without any additional assistance (from the solutions manual or tutor) under time constraints. When you are finished grade the exam, then go back to review the concepts contained in the problems you missed. Repeat until you feel comfortable and confident. 7. Work in groups. Study with your peers! Not only will this make your experience more enjoyable, but you will learn the material better, too. By teaching someone else you will learn the material better, you may learn another way of thinking about a problem, and you will get a more realistic feel for how well you know the material. 8. Ask for help! I hope that you feel comfortable coming to me with questions any time. I am your biggest fan and cheerleader! Additionally, there are other resources available depending on your exact needs: a. Peer tutoring is available through the Peer Tutoring Office. This service is free of charge and on a first come first served basis (684-8832). b. Private tutoring: a list of available graduate student tutors is posted online at http://www.chem.duke.edu/undergraduate/general/tutor.html. Students are responsible (financially and otherwise) for any arrangements they may make with a tutor. c. Organic resource room will be staffed by the recitation TAs for Chem 151. Extremely useful for getting help with recitation material, problems in Loudon or general concepts, etc. Sign-up required. Specific details including times and locations will be posted on Blackboard asap. d. Review sessions will be held at least two days before examinations, by request. e. Academic Skills Instructional Program (ASIP) provides help developing appropriate study habits, exam-taking strategies, and time management skills (684-5917). Also, highly recommended for students who feel they are spending a lot of time studying but still getting low exam scores. Suggested Homework Problems: Chapter 1: 19, 20, 21, 25, 31, 33 Chapter 2: 22 23, 24, 25, 26, 27, 28, 30, 32, 33 Chapter 7: 33a, b, 34, 40, 54 Chapter 3: 18a, b, 19a-d, 20, 22, 24, 25, 26, 29a-c, 34, 38, 40 Chapter 4: 38, 39, 40, 41, 42, 44, 45, 46, 48, 54, 57, 58, 60 Chapter 5: 23a-n, 24 25, 26, 27, 28, 30, 32, 38, 39. 43 Chapter 6: 25, 27, 28, 29, 35, 37, 40, 46 Chapter 7: 31, 32, 36, 37, 41, 44, 48, 50, 51, 58 Chapter 8: 27, 30a,b,d, 33, 35, 37**, 39, 44, 45 Chapter 9: 30, 31, 32, 34, 37, 41, 43, 46, 51, 53, 54, 59, 63 Chapter 10: 31, 32, 36, 37, 40, 41, 49, 50, 53, 55 Chapter 11: 33, 34, 36, 39, 40, 42, 44, 46, 48, 49, 53, 56, 60 Chapter 12: 20, 22, 24, 25, 32 Chapter 13 30, 33, 34, 35, 39, 40, 41, 43, 45, 48, 55 ...
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