Course Meeting Times

Lectures: 3 sessions / week, 1 hour / session


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.


5.13 (Organic Chemistry II)


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.


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.


The grade for the course will be calculated based on the values given below.

Exams 100 points each
Final exam 200 points
Homework 100 points total
Total possible points 600 points


The calendar below provides information on the course's lecture (L) and exam (E) sessions.

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