Chem 634 - Advanced Organic Chemistry - Synthesis and Reactivity

University of Delaware, Fall 2012

Prof. Donald A. Watson

Lecture: Tuesday and Thursday 7-8:30p, Brown Lab (BRL) 116
Discussion Session: Tuesday 8:30-9:30p, Brown Lab (BRL) 116

Office hour: Friday, 10-11a, 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 Date Lecture Topic Notes Reading Lecture Notes
1 Aug 28 Lecture 1 Introduction, Arrow Pushing, Mechanism     Introduction
2 Aug 30 Lecture 2 Nuc. Substitution Chemistry   CS-B 3.1-3.2 Nuc. Sub. Chem
  Sept 4 Lecture 3 Carboxylate Chemistry PS 1 Due CS-B 3.4  
3 Sept 6 Lecture 4 Retrosynthesis, Route Planning   Corey Chs 1-6, handout  
  Sept 11 Lecture 5 Aromatic Sub. Chemistry   CS-B11.1-11.2 Nuc. Aromatic Sub.
4 Sept 13 Lecture 6 Electronic Databases and Searching the Literature Meet in 221 BRL Handout Databases
  Sept 18 Lecture 7 Transition Metal Cat. Cross Coupling Reactions   Heg Chs 1-2, CS-B 7.1, 8.2-8.3, 11.2-11.3 Intro to Organometallics
5 Sept 20 Lecture 8 Transition Metal Cat. Cross Coupling Reactions     Met. Mediated Cross Coupling
  Sept 25 Lecture 9 Alcohol/Ketone Oxidations PS 2 Due CS-B 12.1, 12.5, 12.7 Alcohol/Ketone Oxidations
6 Sept 27 Lecture 10 C=X Reductions, Protecting Groups   CS-B 5.3, 5.6, 5.7, 3.5 and handout (CK 2) Protecting Groups, C=X Reductions
  Oct 2 Lecture 11 Enolate Chemistry   CS-B 1 All Intro to Enolates
7 Oct 4 Lecture 12 Enolate Chemistry     Enolate Stereochem
  Oct 9 Lecture 11 Aldol Reactions   CS-B 2 All; (CK 4) Aldol Chemistry
8 Oct 11 Lecture 12 Aldol Reactions PS 3 Due    
  Oct 16 Lecture 13 Addition of other carbon nuc. to carbonyls   (CK 5)  
9 Oct 18   Midterm Exam Midterm    
  Oct 23 Lecture 14 Alkene Synthesis and Reactivity   CS-B 2.4, 4, 5.1, 5.6 (CK 7,8,9) Alkene Synthesis
10 Oct 25 Lecture 15 Alkene Oxidation     Alkene Oxidation
  Oct 30 Lecture 16 Alkyne Synthesis     Alkyne Rxns, Alkene Reduction
11 Nov 1 Lecture 17 C=C Reductions Outlines & PS 4 Due    
  Nov 6 No Class Radical Chemistry   CS-B 10.3, CS-A 11 Radical Chemistry
12 Nov 13 Lecture 18 Election Day      
  Nov 15 Lecture 19 Radical Chemistry      
13 Nov 20 Lecture 20 Pericyclic Reactions PS 5 Due CS-B 6 (CK 16, 17, 18) Pericyclic Rxns
  Nov 22 Lecture 21 Pericyclic Reactions Term Paper Due    
14 Nov 27 No Class Thanksgiving      
  Nov 29 Lecture 22 Introduction to Organocatalysis      
  Dec 1 Saturday Student Presentations, 9a-2p Presentations    
15 Dec 4 Lecture 23 Strained Rings PS 6 Due CS-B 12.2.1, 10.2 (CK 15) Strained Rings
Finals TBD   FINAL EXAM Final    



Electronic Resouce Guide

Must Know pKa Table

Must Know BDE Table

Old Exams

Midterm 09
Midterm 10
Midterm 11 Exam Key
Midterm 12 Exam Key
Final 09
Final 10
Final 11 Exam Key

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