Course Meeting Times
Lectures: 3 sessions / week, 1 hour / session
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.
| 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.
| 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 |
