Chemistry 204 Organic Chemistry Course Syllabus Spring 2013 Course Goals: Continue to develop an understanding of the structures and structure-activity relationships of organic molecules. Understand and predict reaction mechanisms of organic compounds. Obtain a toolbox of reactions and use these reactions to design the syntheses of organic molecules. Apply the concepts of organic chemistry to original problems. Gain a basic understanding as to how organic chemistry relates to biology. Laboratory Goals: Learn and demonstrate good experimental techniques used in organic chemistry. Develop good recordkeeping methods. Internalize and integrate theoretical principles presented in lecture though practice of these concepts in the laboratory. Experience how chemists do primary literature searches. Learn how to write a detailed laboratory report similar to those found in the primary chemical literature. Instructor Information: Professor Tim Funk e-mail: tfunk@gettysburg.edu phone #: x6348 office location: Science Center room 243 office hours: Anytime Monday through Friday, 8:30 4:15 pm, no appointment necessary, although you re welcome to set one up. Prof. Funk s Spring 2013 Schedule: Monday Tuesday Wednesday Thursday Friday Chem 203 lectures: 8 10 am Lecture Times: Meeting: 11:30 1pm Chem 203 lectures: 8 10 am Faculty Meetings: 4pm on the first and third of each month Chem 203 lectures: 8 10 am Meeting: 10 11am Chem 203 lab discussion: 2:10 3 pm Section A: MWF 8 8:50 am Section B: MWF 9 9:50 am Both Sections: F 2:10 3 pm Masters Hall, room 110 (Mara Auditorium) Masters Hall, room 110 (Mara Auditorium) McCreary Hall, room 115 (Bowen Auditorium)
Lab Sections: Check your schedule for your time and instructor; you must come at your scheduled time. All labs are in the Science Center, room 242. Textbooks and other Materials: Required: Organic Chemistry, eighth edition by L. G. Wade, Jr. and Solutions Manual for Organic Chemistry, 8 th Edition by Jan Simek. THESE ARE THE SAME BOOKS WE USED IN CHEM 203 IN THE FALL 2012 SEMESTER!! Organic Chemistry Laboratory Manual given out for free in Chem 203 in the fall of 2012. If you need a new one please see me. Bound lab notebook (not a spiral or loose-leaf notebook). The composition books sold at the bookstore work well. I suggest NOT getting a notebook with grids. Safety glasses or goggles Course Grades: Three in-class Exams 40% Three Graded Homeworks 15% Laboratory 20% Final Exam 25% Although the laboratory is worth only 20% of your total grade, incompletion of the laboratory portion will result in failure of the course. Exams: Exams will be given during the regular class time and must be taken as scheduled in Masters Hall room 110 unless permission to go elsewhere is requested and granted. Exams will cover material from both lecture and lab. Unless you are otherwise informed, you may only use a calculator and your plastic model kit during exams. Calculators on cell phones may not be used. The final exam will be cumulative and will cover material from the lectures and labs. If there is student interest, a review session (outside of the normal course hours) will be held prior to each exam. If you have an IEAP form, please provide a copy of it to me well in advance of the first exam so the appropriate arrangements can be made.
Homework: There will be two different kinds of homework: 1) Problems in Wade these will be assigned in class and are meant to reinforce the lectures. You should attempt to do these on your own, but you may discuss them with others. These will not be collected or graded, but do not blow them off. You are responsible for knowing how to solve these problems. The answers to these questions are in the Solutions Manual you purchased for the course. 2) Graded Homework these problems will be collected and graded. As with the Wade problems, you should attempt to do these on your own but you may discuss them with others. If you work together, everyone needs to contribute to every problem, otherwise it will be considered an Honor Code violation. If you work with other students or the PLA s, write down the names of the people you worked with on the assignment. The graded homework should be turned in by the due date. A late penalty of a letter grade per day past the due date will be enforced. If it comes down to copying someone else s work and handing the assignment in late, ALWAYS hand it in late. A letter grade penalty is infinitely better than an Honor Code violation. Labs: The laboratory experiments in this course overlap with and add to the lecture topics. Questions on homework assignments and exams will include experimental techniques and other topics covered in the laboratory. The fact that a separate lab discussion section (F 2:10 3 pm) exists shows the importance of understanding the laboratory concepts. The lab portion of Chemistry 204 follows the same format as Chemistry 203. Detailed instructions for how to set up your lab notebook are in the laboratory manual (pages 2 and 3). Notebooks are due in lab the week after an experiment is completed. The graded book will be returned in the boxes in the chemistry lounge at least 2 days before the next experiment. There will be a multi-week project lab in Chemistry 204 which will require you to write a formal lab report. We will talk more about this as the time approaches, and you can find detailed information in the laboratory manual on pages 137 148. A detailed laboratory schedule is located in the laboratory manual on page 108. Be sure to read the assigned reading and the procedure, and answer any pre-lab questions before your lab section. Grading Errors: Any errors in grading must be reported within 1 week of the day an assignment or exam is returned. After this, no changes will be made to your grade.
Assistance Outside of Class: Feel free to come to my office to ask questions anytime. I am on campus and typically in my office from 8:30am until at least 4:15pm every weekday. You don t need to make an appointment, but you can if you would like to. I will not typically be around in the evenings or on weekends, and I will not regularly check my e-mail at those times (but you can always give it a try). We have two Peer Learning Associates for this course. They are excellent resources and friendly people, so feel free to take advantage of their services. Their names, contact information, and review session times are shown below. The review sessions are held in the Chemistry Department lounge on the third floor of the Science Center. Absence: Name E-mail Review session time Gabby Pros prosga01@gettysburg.edu 7 9 pm Wednesday evenings Danielle Rubinstein rubida01@gettysburg.edu 7 9 pm Sunday evenings The best way to do well in this class is to come to and understand the lectures. Your lecture notes should be your primary source of information; therefore, you are expected to attend all lectures. If you must be absent, you are responsible for obtaining the notes from another student. If you must miss an exam or a lab due to extenuating circumstances (illness, family emergency), please notify me (or both me and your lab instructor in the case of labs) as soon as possible. Anticipated absences or conflicts (off-campus athletic competition, academic conferences) should be reported to me well in advance of the event. Honor Code: I take the Honor Code very seriously. It allows us to have a mutual trust and a mutual respect for one another, and that kind of environment is a wonderful one in which to learn. When trust and respect are lost, a community cannot survive. You need to abide by, write out, and sign the Honor Pledge (I affirm that I have upheld the highest principles of honesty and integrity in my academic work and have not witnessed a violation of the Honor Code) on every graded assignment, lab, and exam. Additionally, because the burden ultimately falls on you and your peers to report Honor Code violations, it is important that we are all clear on what constitutes an Honor Code violation. Please obey the following acceptable practices for test-taking:
1. All exams are to be done on your own. No textbooks or any other resources can be used on exams. Molecular model kits and calculators are permitted, but no equations or any other data can be programmed into calculators. You may make model templates (i.e. chiral centers, alkenes,...) beforehand and bring them to the exam. 2. Cell phones must be turned off and put away. You may not use a cell phone as a calculator or to monitor the time (there s a clock at the back of the classroom). The reason for this is to remove any ambiguity about whether or not someone is giving or receiving unauthorized aid using their cell phone or if they re using it for benign reasons. The instructor is under no obligation to accept an exam if any of the acceptable practices are violated. You may receive assistance from the Peer Learning Associates on graded homework assignments, but be sure to include their name(s) on the questions where they were of assistance. Lab assignments may be completed in collaboration with others. Collaboration is intended to be a discussion where everyone contributes intellectually. Blatantly copying answers is a violation of the Honor Code. You must always list the names of people you worked with. The Gettysburg College Honor Pledge states: I affirm that I will uphold the highest principles of honesty and integrity in all my endeavors at Gettysburg College and foster an atmosphere of mutual respect within and beyond the classroom. Calling other s work your own and falsifying data undermine scientific progress and the people you were dishonest to. They also hurt your development as a scientist. These will be treated as Honor Code violations. How to Survive Organic Chemistry: 1) Don t fall behind. 2) Work through all of the assigned problems. 3) Don t fall behind. 4) Study so you truly understand the material, not just so you can regurgitate it. 5) Don t fall behind. Organic chemistry is cumulative by its nature. If you fall behind early, it can be very difficult to catch up. Come to the lectures and understand the lectures. Come to the labs and understand the labs. Do the problems in Wade which support the lecture concepts, and try to do them before the next lecture. Don t just memorize the material, understand it. If you are successful on these fronts, you may find yourself really enjoying the world of organic chemistry.
Proposed Schedule: Date Lecture Topic Reading in Wade Other Homework Jan. 21 Course intro, IR spectroscopy 12-1 12-11 Jan. 23 IR and 13 C NMR spectroscopy 12-12, chapter 13 Jan. 25 13 C NMR Chapter 13 Jan. 28 DEPT, 1 H NMR Chapter 13 Jan. 30 1 H NMR Chapter 13 Feb. 1 1 H NMR Chapter 13 HW#1 distributed Feb. 4 MO Theory and Diels-Alder 15-3, 15-11 Feb. 6 Diels-Alder reaction 15-11 HW#1 due Feb. 8 Diels-Alder reaction 15-11 Feb. 11 alcohols: Williamson ether synthesis, 14-5, 11-5, 11-8 tosylates, PBr 3 Feb. 13 alcohols: alcohol oxidation 11-2, 11-3, 11-4 Feb. 15 alcohols: Alcohol oxidations, NAD +, 11-3, 11-4, 10-8, 10-9 Grignard Feb. 18 Exam 1 Feb. 20 Synthesis of Alcohols: Grignard, hydride reductions 10-8, 10-9, 10-11 Feb. 22 Synthesis of Alcohols: Hydride reductions, NADH 10-11 Feb. 25 Synthesis of 11-2, 11-3, 18-9 Review, nitrile reduction Feb. 27 Imines, imine reduction, 18-15, 19-18, 18-17 acetals Mar. 1 18-17, 18-18 Acetals, protecting groups Mar. 4 18-17-18-18 HW#2 distributed Acetals, protecting groups Mar. 6 18-12 Wittig Mar. 8 Enols, tautomerization, enolates (RO and LDA) 22-1, 22-2 HW#2 due Mar. 11-15 Spring Break Mar. 18 α-alkylation, enamine alkylation 22-3, 22-4
Mar. 20 Enamine alkylation, enamines in biology, aldol condensation Mar. 22 Exam #2 Mar. 25 Aldol condensation Mar. 27 Aldol condensation Mar. 29 Claisen condensation, Dieckmann condensation Apr. 1 Crossed Claisen condensation, β-dicarbonyl compounds as reactants Apr. 3 β-dicarbonyl compounds as reactants Apr. 5 Conjugate addition and Michael reaction Apr. 8 Conjugate addition and Michael reaction, Robinson annulation Apr. 10 Robinson annulation Carbonyl reactions in Apr. 12 biology Carboxylic acids: general info, from 1 alcohols Apr. 15 (review), from hydrolysis of acid derivatives Hydrolysis of carboxylic Apr. 17 acid derivatives Apr. 19 Exam #3 Esters from alcohols and Apr. 22 CA, acid chloride synthesis Esters and amides from acid Apr. 24 chlorides and anhydrides 22-4, 22-7, 22-8 22-8, 22-9 22-9, 22-10, 22-11 22-12, 22-13 22-14, 22-15, 22-16, 22-17 22-15, 22-16, 22-17 22-18 22-18, 22-19 HW#3 distributed 22-19 11-2B, 21-7 21-7 20-10, 20-15 21-5 HW#3 due
Apr. 26 Transesterification, reduction of esters, acids, 21-6, 21-8 amides Apr. 29 Biological molecules: amino acids Chapter 24 May 1 carbohydrates Chapter 23 May 3 lipids Chapter 25 Fri. May 10 Final 6:30-9:30pm