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.
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
