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
Instructor:
Professor T. V. (Babu) RajanBabu (Office: 3073 Evans
Lab; e-mail rajanbabu.1@osu.edu). Office hours: WF
1:30-2:30, and any other time, by appointment.
Teaching Assistants:
Craig Smith (Office: 3083 Evans Lab;
csmith@chemistry.ohio-state.edu)
Hwan Lim (Office 3073 Evans Lab;
hlim@chemistry.ohio-state.edu)
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e-mail:
e-mail:
Prerequisites:
Chemistry 730 is an intermediate level organic chemistry
course. I will try to bridge the gap between sophomorelevel 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.
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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: csbooks@wiley.co.uk)
ISBN 978-0-471-92963-5
(paperback)
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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:
(i) Fuhrhop, J. and Li, G; Organic Synthesis; 3rd
Edition, Verlag Chemie: Weinheim, 2003.
(ii) Smith, M.; March, J. March’s Advanced Organic
Chemistry. Reactions, Mechanisms and Structure, 6th
Ed. Wiley: New York, 2007 (ISBN 978-0-47172091-1).
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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
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documentation to substantiate
circumstances to the instructor.
any
extenuating
Midquarter I
October 15
Monday 7:00 - 9:00 P. M.
Midquarter II
November 14
Wednesday 7:00 - 9:00 P. M. 25 %
Final Examination
December 04
Tuesday 11:30 - 1:30 P. M.
25 %
30 %
Journals homework
Due 10/5, 10/19, 11/2, 11/16, 11/30
10 %
Problem sets Due: as listed on the problem sets 10 %
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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.
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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.
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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
October 15
October 29
Steric and stereoelectronic effects I
Conformation analysis
Steric and stereoelectronic effects II Conformation analysis
Steric and stereoelectronic effects III Enolates and enamines: alkylation I
November 05
Enolates and enamines: alkylation II -
November 12
Reactions of carbon nucleophiles
with carbonyl compounds I
Reactions of carbon nucleophiles
with carbonyl compounds II
Reactions of carbon nucleophiles
with carbonyl compounds III
October 22
November 19
November 26
CS-A Chapter 3, handouts
CS-A Chapter 3, handouts
CS-A Chapter 3, handouts
CS-A Chapter 7
CS-B Chapter 1
CS-A Chapter 7
CS-B Chapter 1
CS-B Chapter 2, handouts
CS-B Chapter 2, handouts
CS-B Chapter 2, handouts
––––––––––––––––––––––––––––––––––––––––––––––
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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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Closed Reserve Books Available in the Library for
Chemistry 730 Autumn 2007
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Parts A and B, 5th Ed.;
Springer: New York, 2007.
Carruthers, W.; Some Modern Methods of Organic Synthesis, 4th Ed.; Cambridge: Univ
Press Cambridge, 2004.
Fuhrhop, J. and Li, G; Organic Synthesis; 3rd Edition, Verlag Chemie: Weinheim, 2003.
Warren, S. Organic Synthesis: The Disconnections Approach, Wiley: New York, 1982.
QD262.W37
Warren, S. Workbook for Organic Synthesis: The Disconnections Approach, Wiley:
New York, 1982. QD262.W35
March, J. Advanced Organic Chemistry, 4th Ed.; Wiley: New York, 1992. QD251.2.M3
Nogradi, M. Stereoselective Synthesis: A Practical Approach; 2nd Ed.; VCH
Publishers: New York, 1995. QD481.N74
House, H. O. Modern Synthetic Reactions, 2nd Ed.; Benjamin: New York, 1972.
QD262.H67
Deslongchamps, Pierre; Stereoelectronic Effects in Organic Chemistry; Pergamon; New
York, 1983. QD481.D47
Fleming, Ian; Selected Organic Syntheses; Wiley: New York, 1973.
Carroll, F. A. Perspectives on Structure and Mechanism in Org. Chemistry QD476.C375
Eliel, E.; Wilen, S. H. “Stereochemistry of Organic Compounds” Wiley: New York,
1994, QD481.E42
Wyatt, P.; Warren, S. Organic Synthesis - Strategy and Control Wiley: Hoeboken, 2006
ISBN 978-0-471-92963-5
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Key Dates
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)
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