Chem 634 - Advanced Organic Chemistry - Synthesis and Reactivity

University of Delaware, Fall 2010

Prof. Donald A. Watson

Lecture: Tuesday and Thursday 7-8:30p, Brown Lab (BRL) 207

Problem Session: Tuesday 8:30-9:30p, TBD
Office hour: Monday, 1-2p, or by appointment (contact via email)


Required Texts

Strategic Applications of Names Reactions in Organic Synthesis
Advanced Organic Chemistry, Part B: Reactions and Synthesis. (5th Edition Recommended) Carey, F. A.; Sundberg, R.

Model Kit

A molecular model kit is required.

Suggested and Reserve Texts

Advanced Organic Chemistry Part A: Structure and Mechanisms Carey, F. A.; Sundberg, R. J.
Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Edition Larock, R. C.
Stereochemistry of Organic Compounds Eliel, E.; Wilel, S. H.
March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th Edition Smith, M. B.; March, J.
Protective Groups in Organic Synthesis, 4th Ed, Greene and Wuts
Transition Metals in the Synthesis if Complex Organic Molecules, 3nd Ed, Hegedus, L. S.
Classics in Stereoselective Synthesis, Erick M. Carreira, Lisbet Kvaerno
The Logic of Chemical Synthesis, Corey, E. J.; Cheng, X.

Topics (Approximate Schedule)

Week 1

Aug 31

Lecture 1

Introduction, Arrow Pushing, Retrosynthesis

Reading: Corey Chapters 1-6


Sept 2

Lecture 2

Electronic Databases and Searching the Literature

Week 2

Sept 7

Lecture 3

Nuc. Substitution Chemistry

C&S B 3.1, 3.2, 3.4


Sept 9

Lecture 4

Carboxylate Chemistry

Week 3

Sept 14

Lecture 5

Nuc. Aromatic Sub. Chemistry


Sept 16

Lecture 6

Introduction to Organometallic Chemistry

Week 4

Sept 21

Lecture 7

Transition Metal Catalyzed Cross Coupling Reactions


Sept 23

Lecture 8

Protecting Groups

Week 5

Sept 28

Lecture 9

Alcohol/Ketone Oxidations


Sept 30

Lecture 10

C=X Reductions

Week 6

Oct 5

Lecture 11

Radical Chemistry


Oct 7

Lecture 12

Radical Chemistry

Week 7

Oct 12

Lecture 11

Enolate Chemistry


Oct 14

Lecture 12

Enolate Chemistry

Week 8

Oct 19


Midterm Exam


Oct 21

Lecture 13

Aldol Reactions

Week 9

Oct 26

Lecture 14

Aldol Reactions


Oct 28

Lecture 15

Aldol Reactions

Week 10

Nov 2

Lecture 16

Introduction to Organocatalysis


Nov 4

Lecture 17

Alkene Synthesis and Reactivity

Week 11

Nov 9

Lecture 18

Alkene Oxidation


Nov 11

Lecture 19

Alkyne Synthesis

Week 12

Nov 16

Lecture 20

C=C Reductions


Nov 18

Lecture 21

Pericyclic Reactions

Week 13

Nov 23

Lecture 22

Pericyclic Reactions


Nov 25

No Class


Week 14

Nov 30

Lecture 23

Strained Rings


Dec 2

Lecture 24

C–H and C–C Bond Activation, time allowing


Dec 4


Student Presentations, 9a-12p

Week 15

Dec 7


Student Presentations

Finals Week


                       FINAL EXAM


Lecture Notes

Week 1
Week 2
Nuc. Sub. Chem
Week 3
Nuc. Aromatic Sub.
Intro to Organometallics
Week 4
Met. Mediated Cross Coupling
Week 5
Protecting Groups
Alcohol/Ketone Oxidations
Week 6

C=X Reductions

Week 7
Intro to Enolates
Enolate Stereochem
Week 8
Week 9
Aldol Chemistry
Week 10
Alkene Synthesis
Alkene Oxidation
Week 11
Alkyne Rxns
Radical Chemistry
Week 12
Pericyclic Rxns
Week 13
Strained Rings
Week 14
M-H Chemistry


Electronic Resouce Guide

Must Know pKa Table

Must Know BDE Table

Old Exams

Midterm 09
Final 09

Useful Links:

pKa Tables:

Evan's pKa Table (Harvard)
Reich's pKa Table (UW Madison)


Nature Chemistry
Chem Comm.
Org. Lett.
Tetrahedon Lett.

Univ. Delaware Chemistry Library:


Reaction and Structure Searching:


Citation Searching:

Web of Science

Listing of review articles complied by Phillip Kocienski (most useful with Endnote format):

Synthesis Reviews