Chemical Structure and Reactivity Fall 2015
Course Instructors: Uttam K. Tambar Office: L3.200 Phone: (214) 648-0580 Email: [email protected]
Joseph Ready, Ph.D. Office: L4.247B Phone: (214)-648-0313 Email: [email protected]
Daniel J. Siegwart Office: ND2.210E Phone: (214) 645-6354 Email: [email protected]
Required (purchase) 1. Molecular Model Kit 2. Carey, F. A.; Sundberg, R. J. “Advanced Organic Chemistry: Part A: Structure and Mechanisms” 3. Carey, F. A.; Sundberg, R. J. “Advanced Organic Chemistry: Part B: Reaction and Synthesis”
Useful References (not necessary to purchase) 1. Corey, E. J.; Cheng, X.-M. "The Logic of Chemical Synthesis" 2. Nicolaou, K. C.; Sorensen, E. J. "Classics in Total Synthesis" vol. 1 3. Eliel, E. L.; Wilen, S. H. "Stereochemistry of Organic Compounds" 4. Hegedus, L. S. "Transition Metals in the Synthesis of Complex Organic Molecules" 5. March, J. "Advanced Organic Chemistry, Fourth Edition"
Library Web Site: http://library.utsouthwestern.edu/index.cfm
Course Grade: Current Literature: 5% Problem Sets: 25% Midterm Exam: 35% Final Exam: 35%
Current Literature: Synthetic chemistry is constantly changing and evolving. In order to keep up with new developments, part of the requirement of this course will be to read new and relevant publications in the primary chemical literature. At the beginning of each class, two of you will be randomly selected to present a synopsis of a recent publication for 3 minutes. The publication should be selected from a recent issue of J. Am. Chem. Soc., Angew. Chem. Int. Ed., or Org. Lett.. In your presentation, include the primary author, institution affiliation and proper reference. This exercise will keep the class current, and it will also help you launch your own database of relevant chemical literature. Your performance in this exercise will impact your grade.
Problem Sets: All Problem Sets will be due at the beginning of class on the designated dates.
Problem Set #1: Tuesday, September 8 Problem Set #2: Tuesday, September 22 Problem Set #3: Tuesday, September 29 Problem Set #4: Tuesday, October 13 Problem Set #5: Tuesday, October 20 Problem Set #6: Tuesday, November 10 Problem Set #7: Tuesday, November 17 Problem Set #8: Tuesday, December 1 Problem Set #9: Tuesday, December 8
FALL 2015
Chemical Structure & Reactivity L4.146 Course Directors: Ready and Tambar Date Time Location Lecturer Topic Comment Problem Sets Aug 25, T 1:00 PM L4.146 Tambar Discussion of Summer Problems Aug 27, Th 1:00 PM L4.146 Tambar Evaluation Test Aug 28, F 1:00 PM L4.162 Tambar Discussion of Evaluation Test Sep 1, T 1:00 PM L4.146 Tambar SN1/SN2 substitution at sp3; s and s* orbitals Sep 3, Th 1:00 PM L4.146 Tambar SeAR/SnAR substitution at sp2 Sep 4, F 1:00 PM L4.162 Tambar Sep 8, T 1:00 PM L4.146 Ready Elimination/fragmentation E1/E2, Grob, Eshenmoser, PS #1 Due (Tambar) HOMO/LUMO of conjugated systems; Sep 10, Th 1:00 PM L4.146 Ready Diels Alder 1 types Sep 11, F 1:00 PM L4.162 Ready Sep 15, T No class L4.146 Lewis Aicd, enantioselective, inverse Sep 17, Th 1:00 PM L4.146 Ready Diels Alder 2 demand Sep 18, F 1:00 PM L4.162 Siegwart Sep 22, T 1:00 PM L4.146 Siegwart Radicals PS #2 Due (Ready) polymerization mechanisms; step- Sep 24, Th 1:00 PM L4.146 Siegwart Polymer 1 growth, chain growth Sep 25, F 1:00 PM L4.162 Siegwart controlled polymerization; catalysis; Sep 29, T 1:00 PM L4.146 Siegwart Polymer 2 physical properties, charaterization PS# 3 Due (Siegwart) Oct 1, Th 1:00 PM L4.146 Ready [3,3] sigmatropic Oct 2, F 1:00 PM L4.162 Siegwart 8-pi, electrocyclic ring opening, Oct 6, T 1:00 PM L4.146 Tambar other pericyclic/photochem Norrish Oct 8, Th 1:00 PM L4.146 Ready Enolate alkylation carbonyl nucleophile Oct 9, F 1:00 PM L4.162 Ready Oct 13, T 1:00 PM L4.146 Tambar Aldol 1 PS# 4 Due (Ready) Oct 15, Th 1:00 PM L4.146 Tambar Aldol 2 Oct 16, F 1:00 PM L4.162 Tambar
Oct 20, T 9:00 AM L4.146 Tambar Carbonyl reduction carbonyl electrophile; LAH, BH3, etc. PS# 5 Due (Tambar) Oct 22, Th no class Oct 23, F 9:00 AM L4.162 Tambar Oct 27, T 9:00 AM L4.146 Tambar Stereoselective carbonyl addition Felkin-Ahn, acyclic conformation Oct 29, Th 9:00 AM L4.146 Tambar Midterm Exam Oct 30, F 9:00 AM L4.162 Tambar Discussion of Midterm Exam Nov 3, T 9:00 AM L4.146 Ready Cu-mediated 1,4- and sub rxns Nov 5, Th 9:00 AM L4.146 Tambar Classical olefin synthesis Wittig, Julia, HWE, Peterson Nov 6, F 9:00 AM L4.162 MacMillan Nov 10, T 9:00 AM L4.146 Tambar Reactions of olefins Br2, OsO4, cycloprop, O3 PS# 6 Due (Ready) Nov 12, Th 9:00 AM L4.146 Tambar Epox 1 acyclic stereocontrol, directed Nov 13, F 9:00 AM L4.162 Tambar Nov 17, T 9:00 AM L4.146 Tambar Epox 2/AD enantioselective, kinetic resolutions PS# 7 Due (Tambar) cation-pi cycliczations; favorski, Nov 19, Th 9:00 AM L4.146 Ready Cationic rearrangements pinacol, Meerwein shifts Nov 20, F 9:00 AM L4.162 Ready Brook, Tamao-Flemming, Evans- Nov 24, T 9:00 AM L4.146 Ready Anionic rearrangements Mislow Nov 26, Th No Class Thanksgiving electron counting, ligands, ox Dec 1, T 9:00 AM L4.146 Ready Organometallics 1 states, structure PS# 8 Due (Ready) Dec 3, Th 9:00 AM L4.146 Ready Organometallics 2 insertions Dec 4, F 9:00 AM L4.162 MacMillan Dec 8, T 9:00 AM L4.146 Ready Organometallics 3 Ox Addns, Red Elim PS# 9 Due (Ready) Dec 10, Th 9:00 AM L4.146 Ready Kinetics 1 Rate law and methods Dec 11, F 9:00 AM L4.162 Ready Dec 15, T 9:00 AM L4.146 Ready Kinetics 2 Examples Dec 17, Th 9:00 AM L4.146 Ready Final Exam
Grading Midterm Exam 35% Final Exam 40% Problem Sets 25%