Chemistry 730
Autumn 1998
MWF 12:30-1:18
Evans 2004
Instructor: Professor T. V. RajanBabu (Office: 3081 Evans Lab; e-mail
RajanBabu.1@osu.edu). Office hours: immediately after class, and by appointment.
Teaching assistant: Sandra Greau (Office: 3073 Evans Lab; e-mail: sgreau@chemistry.ohio-state.edu). Office hours: by appointment.
Texts and study aids:
1. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Parts A and B, 3rd
Ed.; Plenum: New York, 1990.
2. Carruthers, W.; Some Modern Methods of Organic Synthesis, 3rd Ed.; Cambridge:
New York, 1986.
3. Fuhrhop, Jürgen and Penzlin, Gustav; Organic Synthesis; 2nd Edition, Verlag
Chemie: Weinheim, 1994.
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 reaction types which you will encounter in this course and in 832 and 833.
I have placed several other books on 'closed reserve' at the library and you will find them useful. In particular, Organic Synthesis: The Disconnections Approach, andWorkbook for Organic Synthesis: The Disconnections Approach, are good to study on your own. Two excellent reference books well worth adding to your personal library are (i) Smith, M. B. Organic Synthesis, McGraw-Hill: New York (1994) and (ii) March, J.
Advanced Organic Chemistry, 4th Ed.; Wiley: New York, 1992.
A good set of molecular models is highly recommended. I strongly encourage you to make model-building and three-dimentional 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.
Prerequisites: 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 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 the basics of bonding in organic compounds, stereochemistry, chemistry of alkenes,
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alkynes and carbonyl compounds from a good undergraduate book. I recommend
Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry,
Macmillan: New York (1992), which has been placed under closed reverve in the library.
Withdrawal: The last date for withdrawal from this class without a W is October 9 and with a W is November 6. The University will not generally allow withdrawal from the course after November 6.
Examinations and Grading:: Your grades will be determined primarily by your performance in the examinations. There will be two mid-quarter examinations and a final. The final examination will be comprehensive.
No makeup examinations will be given. 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 documetation to substantiate an extenuating circumstance to the lecturer during the first two weeks of the class.
Midquarter I October 19 Monday 6:00 - 8:00 P. M.
Midquarter II
25 %
November 16 Monday 6:00 - 8:00 P. M.
25 %
Final examination December 07
Journals homework
Monday 11:30 - 2:30 P. M.
Due 10/2, 10/16, 10/30, 11/13, 11/30
Problem sets Due 10/9, 10/23, 11/06, 12/4
40 %
5 %
5 %
Journal Homework: 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 paper every other week on the
last day of the week, starting on October 2 (total of 5 submissions). 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. The journals you should examine are: J. Am. Chem. Soc., J. Org. Chem., Chem. Commun., Tetrahedron,
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Tetrahedron Lett. Synthesis, and Angew. Chem. Int. Ed. Engl. You may use any material between 1980 to 1998.
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. You are urged to use the books that are on reserve, as well as other library sources.
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Tentative Reading assignments (CS = Carey and Sundberg; Car = Carruthers)
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Week of Topic Reading
––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––––
September 23
September 28
October 5
Stereochemical Principles
Stereochemical principles
Conformation analysis
CS-A Chapter 2 &
Handouts
-do-
CS-A Chapter 3 &
Handouts
October 12
October 19
Steric and steroelectronic effects I
Conformation analysis
Steric and steroelectronic effects II
Enolates and enamines: alkylation I
-do-
CS-B Chapter 1
CS-A Chapter 7
Car 1-48 & handouts
October 26
November 2
November 9
November 16
November 23
Enolates and enamines: alkylation II -do-
Reactions of carbon nucleophiles CS-B Chapter 2 & with carbonyl compounds I
Reactions of carbon nucleophiles
Handouts, Car 48-63 with carbonyl compounds II
Reactions of carbon nucleophiles
-do- with carbonyl compounds III -do-
Functional group interconversion by CS-B Chapter 3 &
November 30 nucleophilic substitution I CS-A Chapter 5
Functional group interconversion by nucleophilic substitution II -do-
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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.
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Key Dates
September 23
October 9
October 19
November 11
November 16
November 27
December 04
December 07
First day of class
No class, makeup will be arranged
Ist Mid-quarter examination (6:00 - 8:00 P. M.)
Veterans day, no class
2nd Mid-quarter examination (6:00 - 8:00 P. M.)
Thanksgiving, no class
Last day of class
Final examination (11:30 - 2:30)
The following books have been placed on reserve for you in the library.
1.
2.
Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Parts A and B, 3rd Ed.;
Plenum: New York, 1990.
Carruthers, W.; Some Modern Methods of Organic Synthesis, 3rd Ed.; Cambridge:
New York, 1986.
3. Fuhrhop, Jürgen and Penzlin, Gustav; Organic Synthesis, 2nd Ed.; Verlag
Chemie: Weinheim, 1994.
4. Warren, S. Organic Synthesis: The Disconnections Approach, Wiley: New York,
1982.
5. Warren, S. Workbook for Organic Synthesis: The Disconnections Approach, Wiley:
New York, 1982.
6. Smith, M. B. Organic Synthesis, McGraw-Hill: New York (1994).
7. March, J. Advanced Organic Chemistry, 4th Ed.; Wiley: New York, 1992.
8. Nogradi, M. Stereoselective Synthesis: A Practical Approach, 2nd Ed.; VCH
Publishers: New York, 1995,
House, H. O. Modern Synthetic Reactions, 2nd Ed.; Benjamin: New York, 1972. 9.
10. Deslongchamps, Pierre; Stereoelectronic Effects in Organic Chemistry; Pergamon;
New York, 1983.
11. Fleming, Ian; Selected Organic Syntheses; Wiley: New York, 1973.
12. Bindra, J. S.; Bindra, R. Creativity in Organic Synthesis, Vol 1; Academic Press:
New York, 1975.
13. Anand, N.; Bindra, J. S.; Ranganathan, S. Art in Organic
Synthesis, 2nd Ed.; Wiley: New York, 1988.
14. Streitwieser, A. Introduction to Organic Chemistry, 4th Ed.; McMillan: New
York, 1992 and Study Guide.
15. Eliel, E.; Wilen, S. Sterochemistry of Organic Compounds ; Wiley: New York, 1982.
16. Carroll, F. A. Structure and Mechanism in Organic Chemistry ; Brrokes-Cole: New
York, 1982.
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