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Chemistry 730, Autumn 2007: Intermediate Organic Chemistry
Tentative Syllabus and Course Outline
CHEM 730 Call no. 04892-3 McPherson Laboratory1040 MWF 12:30-1:18
Professor T. V. (Babu) RajanBabu (Office: 3073 Evans Lab; e-mail email@example.com). Office hours: WF 1:30-2:30, and any other time, by appointment.
Craig Smith (Office: 3083 Evans Lab; e-mail: firstname.lastname@example.org)
Hwan Lim (Office 3073 Evans Lab; e-mail: email@example.com)
Chemistry 730 is an intermediate level organic chemistry course. I will try to bridge the gap between sophomore-level organic chemistry and the more advanced courses that many of you will be taking in the up-coming quarters. In general, you are expected to have mastered the topics covered in undergraduate organic chemistry. Before we start discussing more involved topics, I urge you to review from a good undergraduate book the basics of bonding in organic compounds, stereochemistry, definitions and terminology related to chirality, chemistry of alkenes, alkynes, alcohols, aromatic and carbonyl compounds. I recommend Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry, Macmillan: New York (1992), which has been placed under closed reserve in the library.
Texts and Study Aids Chem 6420 (Au 2012)
1. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 5th Ed. Parts A and B, Kluver Academic: New York, 2007. Also useful for Chem 6410, 6430, and 7430.
2. Carruthers, W.; Coldham, I. Modern Methods of Organic Synthesis, 4th Ed.; Cambridge University Press: Cambridge, 2004.
3. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry University Science Books: Suasalito, 2006. Also useful for Chem 6410, 6430, and 7430.
4. Wyatt and Warren: Organic Synthesis, Strategy and Control, Wiley: Chichester (2007) (web: firstname.lastname@example.org) ISBN 978-0-471-92963-5 (paperback)
I plan to follow the contents of the specific chapters of Carey and Sundberg as indicated in the following pages. Additional references will be added to supplement and update the text. Carruthers' book gives an excellent summary of several important reactions, which you will encounter in this course, and also in Chemistry 832 and 833.
I have placed several other books on 'closed reserve' at the library (see at the end of this syllabus) and you will find them useful for further reading and in solving the problem sets. In particular, Organic Synthesis: The Disconnections Approach, and Workbook for Organic Synthesis: The Disconnections Approach, are good to study on your own. Two excellent other reference books well worth adding to your personal library are:
(ii) Smith, M.; March, J. March’s Advanced Organic Chemistry. Reactions, Mechanisms and Structure, 6th Ed. Wiley: New York, 2007 (ISBN 978-0-471-72091-1).
Molecular Models: You should purchase a good set of molecular models. I strongly encourage you to make model-building and three-dimensional al visualization of intermediates an integral part of your study habits. You may use models during examinations; I do expect, in your answers, clear, intelligible three-dimensional drawings, if they are appropriate.
Withdrawal: The last date for withdrawal from this class without a W is October 5 and with a W is November 2. The University will not generally allow withdrawal from the course after November 2.
Examinations and Grading: Your grades will be determined primarily by your performance in the examinations and homework assignments. There will be two mid-quarter examinations and a final. The final examination will be comprehensive. Last year’s grade distribution (Total: 25 students): A 6; B+ 6; B 9; B_ 1; C 3.
No makeup examinations are planned. You must take these examinations at the assigned time. For students having a class conflict, an early examination will be given at 4.00 P. M. on the same day. A special time maybe requested if you still have a conflict. To take an early examination or to take the examination at a special time, you must submit a copy of your class schedule or documentation to substantiate any extenuating circumstances to the instructor.
October 15 Monday 7:00 - 9:00 P. M. 25 %
November 14 Wednesday 7:00 - 9:00 P. M. 25 %
December 04 Tuesday 11:30 - 1:30 P. M. 30 %
Due 10/5, 10/19, 11/2, 11/16, 11/30 10 %
Problem sets Due: as listed on the problem sets 10 %
Journal Homework: This will consists of two parts. During your graduate study you are expected to read widely from the original chemical literature. In an effort to initiate you into this activity, you will be required to submit a one-page (no longer) abstract of one article of your choice every other week on the last day of the week, starting on October 6 (total of 5 submissions). The journals you should examine are: J. Am. Chem. Soc., J. Org. Chem., Org. Lett., Chem. Commun., Tetrahedron Lett., Synlett, Synthesis, and Angew. Chem. Int. Ed. You may use any material between 1990 to 2007. The abstract should be neatly handwritten and should use chemical structure drawings as much as possible. Briefly summarize in a paragraph or less the salient points of the paper, including (a) why the work is significant (b) in what way it is novel, and (c) what are the limitations of the chemistry, if this deals with new synthetic methodology. To critically assess the work, you should look-up several of the references cited in the paper. Attach the original article to your submission.
The second part of your literature report should be a concise description of a summary of an article, relevant to Chem 730, which will be distributed to you to read and analyze according to the schedule shown above. Do not photocopy major Schemes and Tables from the papers into your abstracts. Represent the conclusions in your own words.
Problem sets: Four problem sets will be distributed in class and they will be graded and returned to you. The problem sets may cover some material that we will not have time to go over in class, so it is important that you work all the problems. You will be responsible for the reactions covered in the problem sets. I would encourage you to solve the problems individually at first, before seeking help from your classmates or the TAs. You are urged to use the books that are on reserve, as well as other library sources.
Tentative Schedule (CS = Carey and Sundberg)
Week of Topic
September 19 Stereochemical Principles CS-A Chapter 2, handouts
September 24 Stereochemical principles CS-A Chapter 2, handouts
October 01 Stereochemical principles/Conformational
analysis CS-A Chap. 2, 3,handouts
October 08 Steric and stereoelectronic effects I CS-A Chapter 3, handouts
October 15 Conformation analysis
Steric and stereoelectronic effects II - CS-A Chapter 3, handouts
October 22 Conformation analysis
Steric and stereoelectronic effects III - CS-A Chapter 3, handouts
October 29 Enolates and enamines: alkylation I CS-A Chapter 7
CS-B Chapter 1
November 05 Enolates and enamines: alkylation II - CS-A Chapter 7
CS-B Chapter 1
November 12 Reactions of carbon nucleophiles
with carbonyl compounds I CS-B Chapter 2, handouts
November 19 Reactions of carbon nucleophiles
with carbonyl compounds II CS-B Chapter 2, handouts
November 26 Reactions of carbon nucleophiles
with carbonyl compounds III CS-B Chapter 2, handouts
Reading: You are responsible for all the topics in the chapters identified in bold, even though I may not be able to cover some topics because of time constraints. I expect you to keep your reading ahead of the lecture. You should also read the handouts and the original literature citations given during the class.
Closed Reserve Books Available in the Library for Chemistry 730 Autumn 2007
1. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Parts A and B, 5th Ed.; Springer: New York, 2007.
2. Carruthers, W.; Some Modern Methods of Organic Synthesis, 4th Ed.; Cambridge: Univ Press Cambridge, 2004.
3. Fuhrhop, J. and Li, G; Organic Synthesis; 3rd Edition, Verlag Chemie: Weinheim, 2003.
4. Warren, S. Organic Synthesis: The Disconnections Approach, Wiley: New York, 1982. QD262.W37
5. Warren, S. Workbook for Organic Synthesis: The Disconnections Approach, Wiley: New York, 1982. QD262.W35
6. March, J. Advanced Organic Chemistry, 4th Ed.; Wiley: New York, 1992. QD251.2.M3
7. Nogradi, M. Stereoselective Synthesis: A Practical Approach; 2nd Ed.; VCH Publishers: New York, 1995. QD481.N74
8. House, H. O. Modern Synthetic Reactions, 2nd Ed.; Benjamin: New York, 1972. QD262.H67
9. Deslongchamps, Pierre; Stereoelectronic Effects in Organic Chemistry; Pergamon; New York, 1983. QD481.D47
10. Fleming, Ian; Selected Organic Syntheses; Wiley: New York, 1973.
11. Carroll, F. A. Perspectives on Structure and Mechanism in Org. Chemistry QD476.C375
12. Eliel, E.; Wilen, S. H. “Stereochemistry of Organic Compounds” Wiley: New York, 1994, QD481.E42
13. Wyatt, P.; Warren, S. Organic Synthesis - Strategy and Control Wiley: Hoeboken, 2006 ISBN 978-0-471-92963-5
September 19 First day of class
October 15, Monday First Mid-quarter examination (7:00 - 9:00 P. M.)
November 9 Veterans day, no class
November 14, Wednesday 2nd Mid-quarter examination (7:00 - 9:00 P. M.)
November 23 Thanksgiving/Columbus Day, no class
November 30 Last day of class
December 04, Tuesday Final examination (11:30 - 1:30)