Chem 634 - Advanced Organic Chemistry - Synthesis and Reactivity

University of Delaware, Fall 2010

Prof. Donald A. Watson

dawatson-at-udel.edu

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)

Syllabus

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

Thanksgiving

Week 14

Nov 30

Lecture 23

Strained Rings

 

Dec 2

Lecture 24

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

 

Dec 4

Saturday

Student Presentations, 9a-12p

Week 15

Dec 7

 

Student Presentations

Finals Week

 

                       FINAL EXAM

 

Lecture Notes

Week 1
Introduction
Databases
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
(Updated)

Week 7
Intro to Enolates
Enolate Stereochem
Week 8
Midterm
 
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
 

Handouts

Electronic Resouce Guide

Must Know pKa Table

Must Know BDE Table

Old Exams

Midterm 09
Exam
Key
Final 09
Exam
Key


Useful Links:

pKa Tables:

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

Journals:

Science
Nature
Nature Chemistry
JACS
ACIE
Chem Comm.
Org. Lett.
Tetrahedon
Tetrahedon Lett.

Univ. Delaware Chemistry Library:

Website

Reaction and Structure Searching:

Scifinder
Reaxys

Citation Searching:

Web of Science

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

Synthesis Reviews