Chem 634 Fall 2010

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)

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

Problem Sets

	Problem Set	Key
Week 1	PS 1	Key
Week 2	PS 2	Key
Week 3	PS 3	Key
Week 4	--	--
Week 5	--	--
Week 6	PS 4	Key
Week 7	--	--
Week 8	Midterm	Key
Week 9
Week 10	PS 5	Key
Week 11	PS 6	Key
Week 12	--	--
Week 13	PS 7	Key
Week 14	PS 8	Key
Final Exam	Final	Key

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