Movassaghi, Mohammad, 5.43 Advanced Organic Chemistry, Spring 2007. (Massachusetts Institute of Technology: MIT OpenCourseWare), http://ocw.mit.edu (Accessed 09 Jul, 2010). License: Creative Commons BY-NC-SA
These two adamantane structures are enantiomers, or mirror images, of each other. (Image by MIT OpenCourseWare.)
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.
Syllabus
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 |
|