Chem 634 - Advanced Organic Chemistry - Synthesis and Reactivity

University of Delaware, Fall 2009

Prof. Donald A. Watson

dawatson@udel.edu

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

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

Syllabus

**************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)

Topics
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

MIDTERM EXAM

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

Dec

          

    FINAL EXAM

 

Lecture Notes

Week 1
Intro
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
Midterm
-----
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)

Journals:

Science

Nature

JACS

ACIE

Chem Comm.

Org. Lett.

Tetrahedon

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.
Beilstein

Citation Searching:

Web of Science

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

Synthesis Reviews