Chem 223
Advanced Organic Reactions
Chemistry 223
C. J. Rizzo
SC 7662
322-6100
email: c.j.rizzo@vanderbilt.edu
Prerequisite: Chem 220 a and b (Organic Chemistry) and
preferably Chem 220c or an equivalent course.
Texts: This course will largely be from class notes
which will be available prior to the lecture. There are links
to PDF versions of the class notes below which can be read and
printed with Adobe
Acrobat Reader 3.0. In addition, a hard copy is available
in room SC 7620 for you to photocopy. I will assign problem from
Carey & Sundberg Part B which we will go over.
- F.A. Carey and R.A. Sundberg “Advanced Organic Chemistry,
Part B: Reactions and Synthesis (3rd Edition).” Plenum Press
1991 (required) - J. A. March , M. B. Smith”Advanced Organic Chemistry.
Reactions, Mechanisms and Structure (Fifth Edition), J. Wiley
& Sons, 2001 (recommended) - M. B. Smith, “Organic Synthesis.” McGraw-Hill 1992
(recommended) for a list of correction to the 3rd printing of
this book see: http://orgchem.chem.uconn.edu/home/oserrors.html
Exams: Two mid term exams and a Final. The exams will
be sometime in the middle of Feb and end of March. The exact dates
and time will be arrange as the exam date nears. The Final
Exam is scheduled for Sat. April 28, 2001 at 3:00 pm. No Alternate
Final will be offered. Please make your travel plans accordingly.
Grading: Each exam with count equally toward the final
grade. There will also be at least two take home assignments.
The total for these two assignments will be the same as one exam.
Office Hours: I will have open office hours. If you
would like to see me, simply stop by my office. While this does
not guarantee that I will be available, I will do everything possible
to see you or make arrangements to meet at a mutually convenient
time. Making an appointment to see may be most effective.
Past Exams:
Exams Spring 2001
Exam 1: Grade
distribution
Exam 2: Grade
distribution
A. Introduction- Selectivity
in Organic Chemistry (8/20/98)
B. Functional Group Chemistry:
1. Oxidations
(8/23/98)
Carey & Sundberg: Ch. 12 problems: 1a,c,e,g,n,o,q; 2a,b,c,f,g,j,k;
5; 9a,c,d,e,f,l,m,n; 13
2. Reductions (8/25/98)
Carey
& Sundberg Ch. 5 problems: 1a,b,c,d,f,h,j; 2; 3a-g, n,o; 4b,j,k,l;
9; 11;
3. Protecting
Groups (9/2/98)
Carey & Sundberg Ch. 13.1problems # 1; 2; 3a, b, c ;
4. C-C
Bond Formation (10/9/98)
C&S: Ch. 1, 2.1, 2.2 problems Ch 1: 1; 2; 3, 7; 8a-d; 9; 14
Ch. 2: 1; 2; 4
C&S:
Chapt. 7, 8, 9 problems ch 7: 1; 2; 3, 6; 13 Ch. 8: 1; 2
C&S
Chapt. 6.5, 6.6, 6.7 # 1e,f,h,op
5. C=C
Bond Formation (9/28/98)
C&S Ch. 2 # 5,6,8,9,12
6. C%C
Bond Formation (10/23/98)
7. Other
Functional Group Interconversions (10/23/98)
C&S Chapter 3 #1; 2; 4a,b, e; 5a, b, d; 6a,b,c,d; 8
C. Ring Chemistry:
1. Three-membered
Rings (10/23/98)
2. Four-membered
Rings (10/23/98)
3. Baldwin’s
Rules for Ring Closure (10/23/98)
J. Chem. Soc. Chem. Commun. 1976, 734, 736, 738.
J. Org. Chem. 1977, 42, 3846.
4. Five-membered
Rings (11/17/98)
5. Six-membered
Rings (12/1/98)
6. Medium
Sized Rings (12/1/98)
7. Large Rings
Other Reference Material
R.K. Mackie, D.M. Smith, R.A. Aitken “Guidebook to Organic
Synthesis (2nd Edition),” Longman Scientific & Technical,
1990
W. Carruthers “Some Modern Methods of Organic Synthesis
(2nd Edition),” Cambridge University Press, 1978
H.O. House “Modern Synthetic Reactions (second edition),”
Benjamin-Cummings, 1972
T.W. Greene, P.G.M. Wuts, “Protective Groups in Organic
Synthesis (2nd Edition),” J. Wiley & Sons, 1991.
R.C. Larock “Comprehensive Organic Transformations,”
VCH Publishers, 1989.
J. Fuhrhop, G. Penzlin “Organic Synthesis. Concepts, Methods,
Starting Materials,” Verlag Chemie, 1984.
E. L. Eliel, S. H. Wilen, L. N. Mander “Stereochemistry
of Organic Compounds,” J. Wiley & Sons, 1994.
Fieser & Fieser “Reagents for Organic Synthesis,”
16 volumes, J. Wiley & Sons.
Harrison & Harrison, et al. “Compendium in Organic
Synthetic Methods,” 6 volumes, J. Wiley & Sons.
S. Patai “The Chemistry of Functional Groups,” 27
volumes, J. Wiley & Sons.
“Organic Reaction,” 46 volumes, J. Wiley & Sons.
Barton & Ollis “Comprehensive Organic Chemistry,”
6 volumes, Pergamon Press 1979.
Trost & Fleming “Comprehensive Organic Synthesis.
Selectivity, Strategy, & Efficiency in Modern Organic Chemistry,”
9 volumes, Pergamon Press, 1991.
L. A. Paquette “Encyclopedia of Reagents for Organic Synthesis,”
8 volumes, J. Wiley & Sons, 1995