Organic Structural Methods Chemistry 136, Spring 2012 Office Hours: Instructor: In lab or my office at any time. E-­‐mailed questions are welcome. Prof. Yves Rubin (yrubin.ucla@gmail.com) Lecture: Labs: Text: Thursday, 12:00 -­‐ 1:40 PM, Young Hall, Room 3069 Section 1A: Tuesday / Thursday, 2 -­‐ 6 p.m., Young Hall, Room 6110 Section 1B: Wednesday / Friday, 2 -­‐ 6 p.m., Young Hall, Room 6110 Section 1C: Wednesday / Friday, 2 -­‐ 6 p.m., Young Hall, Room 6072 "Introduction to Spectroscopy" (click on title for website link) by Pavia, Lampman, Kriz, Vyvyan, 4th Edition, Brooks/Cole Cengage Learning Course Topics and Exams: Topic Reading Introduction, Purification, Lab Techniques Lecture and handouts Infrared Spectroscopy, Example Problems PLK Chapter 2 Introduction to NMR PLK Chapter 3 NMR Coupling Constants and Advanced Techniques PLK Chapters 5, 6 NMR Carbon-­‐13 PLK Chapter 4 MIDTERM EXAM (Thursday May 10, 2012 in class and open-­‐book) 2-­‐Dimensional NMR: PLK Chapter 10 Mass Spectrometry: PLK Chapters 8 FINAL EXAM (Monday, June 11, 2012, 6:30 PM -­‐ 9:30 PM) Grading: Lab Reports (50 pts for 1st, 75 each for 2nd to 5th) 350 points 4 Problem Sets (50 pts each for IR, NMR, adv. NMR, MS) 200 points Midterm Exam 100 points Final Exam 200 points Total 850 points Other useful sources: • High Resolution NMR Techniques in Organic Chemistry by T.D.W. Claridge; Pergamon, 2nd Edition, 2009 • Structure Elucidation by NMR in Organic Chemistry by Breitmaier; Wiley, 3rd Edition, 2002 • Spectroscopic Methods in Organic Chemistry by Hesse, Meier, Zeeh; Thieme, 2nd Edition, 2008 • Vogel's Textbook of Practical Organic Chemistry by Vogel; Prentice Hall, 5th Edition, 1996 Laboratory Guidelines The laboratory component of this course focuses on the determination of unknown chemical structures using physical (m.p., b.p. color, etc) and spectroscopic methods (IR, NMR, MS). There is no specific “recipe” or directions provided to carry out these experiments, except for Experiment 1. Guidelines and techniques will be given in class, but you will need to put yourself in a “detective” frame of mind and devise purification and analytical methods for each compound. The TAs will be there to provide guidance, but they are “forbidden” to give you specific recipes or directions. The whole purpose of this course is to teach you how to think creatively to solve problems, which seems quite unsettling at first, but the best way to learn. Except for Lab Report 1, all lab reports will consist of a completed “Unknown Report Sheet”, which must include original spectra acquired by yourself, as well as a clear analysis of the data (see example report online). Teaching Assistants: Christopher Day (day@chem.ucla.edu) Nicholas Knutson (nsk2@chem.ucla.edu) Beijia Li (bli@chem.ucla.edu) Caitlin Decker (cait.decker@gmail.com) Minoo Sedighi (sedighi@chem.ucla.edu) Schedule of Unknowns and Lab Reports: Experiment Type Distribution/Start Date Report Due Date1 1 April 3/4 Thursday, April 192 April 10/11 Thursday, May 3 April 25/26 Thursday, May 17 2 3 Qualitative Analytical Tests (1 g) Mixture of 2 unknowns (solid, 500 mg) Mixture of 2 unknowns (solid or liquid, 200 mg) 4 Natural Product Extraction May 8/9 Thursday, May 313 5 Artificial Flavor Synthesis May 22/23 Monday, June 113 Notes: 1 All reports are due in class at the beginning of lecture, 10 pts will be taken off if late! 2 This is not a full lab report, use the “Organic Qualitative Analysis” handout to prepare this report, which is available online in Word format. 3 In addition to standard characterization, you will be expected to run one of your own 2D experiments (COSY, NOESY, HMQC, or HMBC) on only one of your samples from experiments 4 or 5.