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Description
This course deals with the application of structure and theory to the study of organic reaction mechanisms: stereochemical features including conformation and stereoelectronic effects; reaction dynamics, isotope effects and molecular orbital theory applied to pericyclic and photochemical reactions; and special reactive intermediates including carbenes, carbanions, and free radicals.
Prerequisites
5.13 (Organic Chemistry II)
Textbooks
Carey, F. A., and R. J. Sundberg. Advanced Organic Chemistry, Part A: Structure and Mechanisms. 4th ed. New York, NY: Springer, 2000. ISBN: 9780306462429.
Joule, J. A., and K. Mills. Heterocyclic Chemistry. 4th ed. Malden, MA: Blackwell Science, 2000. ISBN: 9780632054534.
Problem Sets
There will be eight problem sets, to be handed in.
Exams
There will be three exams worth 100 points each given during the term and a cumulative final exam worth 200 points given during final exam period.
Grading
The grade for the course will be calculated based on the values given below.
Grading criteria.
| ACTIVITIES |
WEIGHTS |
| Exams |
100 points each |
| Final exam |
200 points |
| Homework |
100 points total |
| Total possible points |
600 points |
Calendar
The calendar below provides information on the course's lecture (L) and exam (E) sessions.
Course calendar.
| SES # |
TOPICS |
KEY DATES |
| L1-L4 |
Stereochemistry |
Problem set 1 out in Lec #3 |
| L5-L7 |
Elucidating reaction mechanisms |
Problem set 1 due in Lec #6
Problem set 2 out in Lec #6
|
| L8-L9 |
Free radical reactions |
Problem set 2 due in Lec #9 |
| E1 |
Exam 1 |
|
| L10-L13 |
Free radical reactions (cont.) |
Problem set 3 out in Lec #11 |
| L14-L15 |
Photochemistry |
Problem set 3 due in Lec #14
Problem set 4 out in Lec #14
|
| L15-L16 |
Carbenes |
|
| L17 |
Total synthesis |
Problem set 4 due |
| E2 |
Exam 2 |
|
| L18 |
Total synthesis (cont.) |
|
| L19 |
Intro to heterocycles/pyradine |
Problem set 5 out |
| L20 |
Pyridine/directed metallation |
|
| L21 |
Pyridine, quinoline (quinine), isoquinoline |
|
| L22-L23 |
Pyrroles |
Problem set 5 due in Lec #23
Problem set 6 out in Lec #23
|
| L24-L25 |
Azoles |
|
| L26-L27 |
Indoles |
Problem set 6 due in Lec #26
Problem set 7 out in Lec #26
|
| L27-L29 |
Brief intro to organometallic chemistry |
|
| L30 |
Indoles/OM indoles |
Problem set 7 due
Problem set 8 out
|
| E3 |
Exam 3 |
|
| L31 |
Furan, thiophene, polythiophene |
|
| L32 |
Pyridazine, pyrimidine, pyrazine and related reading |
|
| L33 |
Other important aromatic heterocycles |
|
| L34-L35 |
Synthesis/chemistry of industrially imported heterocycles |
Problem set 8 in Lec #34 |
| L36 |
Biosynthesis of heterocycles |
|
| E4 |
Final exam |
|