Chem 634 - Advanced Organic Chemistry - Synthesis and Reactivity

University of Delaware, Fall 2009

Prof. Donald A. Watson

Lecture: Thursday 7-10p, Colburn Lab (CLB) 109

Office hour: Friday 12-1p, LDL 205, or by appointment (contact via email)


**************Final Exam Date**************************

Monday Dec 14th, 3:30-6:30p, CLB102

Similar to the midterm, note cards will be allowed on the Final Exam
for 634. I do not care if they are on proper notecards or sheets of
paper. The only rules are: they must be hand written (by you) and they
can not simply be your notes from class. I reserve the right to inspect
the cards during the exam to make sure this is adhered to.

Model Sets are also allowed.


Required Texts

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

Suggested and Reserve Texts

Organic Synthesis: Strategy and Control. Wyatt, P.; Warren, S.
Workbook for Organic Synthesis: Strategy and Control.  Wyatt, P.; Warren, S.
Advanced Organic Chemistry ยท 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, 2nd Ed, Hegedus, L. S.


Topics (Approximate Schedule)

Suggested Reading

Week 1

Sept 3rd

Lecture 1

Introduction, Nucleophilic Substitution Chemistry

C&S B 3.1-3.2, 3.4

Week 2

Sept 10th

Lecture 2

Intro to Organometallic Reactions

Hegedus Ch. 1-2, C&S B 7.1, 8.2-8.3, 11.2-11.3

Week 3

Sept 17th

Lecture 3

Protecting Groups, Alcohol and Carbonyl Oxidation

C&S B 3.5, 7.1, 7.3.1, 12.1, 12.5, 12.7

Week 4

Sept 24th

Lecture 4

Enolate Alkylations

C&S B 12.1, Ch 1 all

Week 5

Oct 1st

Lecture 5

Reductions of Carbonyls and Imines

C&S B 2 all and 5.3, 5.6, 5.7

Week 6

Oct 8th

Lecture 6

Reactions of Carbonyls with Carbon Nucleophiles

Week 7

Oct 15th


Week 8

Oct 22th

Lecture 7

Alkene Synthesis and Reactivity

C&S B 2.4, 4, 5

Week 9

Oct 29th

Lecture 8

Alkyne Synthesis and Reactivity

Carreira 7

Week 10

Nov 5th

Lecture 9

Pericyclic Reactions (Part 1)

C&S B 6 all

Week 11

Nov 12th

Lecture 10

Pericyclic Reactions (Part 2)

C&S B 6 all

Week 12

Nov 19th

Lecture 11

Strained Rings

C&S B 12.2.1,10.2

Week 13

Nov. 24th

Lecture 12

M-H Chemistry

Week 14

Dec 3rd

Lecture 13

Radical Reactions

C&S B 10.3, C&S A 11

Finals Week





Lecture Notes

Week 1
Nuc. Sub. Chem
Week 2
Nuc. Arom. Sub.
Intro Organomet. Chem.
Week 3
Metal Med. Sub Chem
Week 4
Protecting Groups
Alcohol/Ketone Oxidation
Week 5
Intro to Enolates
Enolate Stereochem
Week 6
C=X Reductions
Week 7
Week 8
Aldol Chemistry
Week 9
Alkene Synthesis
Alkene Oxidation
Week 10
Alkyne Syn. and C=C Reductions
Week 11
Pericyclic Reaction
Week 12
Strained Rings (Updated)
Week 13
Metal Hydride Chem
Week 14
Radical Chemistry



Useful Links:

pKa Tables:

Evan's pKa Table (Harvard)

Reich's pKa Table (UW Madison)






Chem Comm.

Org. Lett.


Tetrahedon Lett.

Important Online Resources (Not to be used on Problem Sets):

Reaction and Structure Searching:

Scifinder - note: updated Friday 9/4 to link to instrutions for new web version.

Citation Searching:

Web of Science

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

Synthesis Reviews