Chem 634 Fall 2011

Chem 634 - Advanced Organic Chemistry - Synthesis and Reactivity

University of Delaware, Fall 2011

Prof. Donald A. Watson

dawatson-at-udel.edu

Lecture: Tuesday and Thursday 7-8:30p, Brown Lab (BRL) 207
Discussion Session: Tuesday 8:30-9:30p, Brown Lab (BRL) 207

Office hour: Friday, 9-10a, 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	1-Sep	Lecture 1	Introduction, Arrow Pushing, Mechanism			Intro and Retrosynthesis
2	6-Sep	Lecture 2	Nuc. Substitution Chemistry	PS 1 Due	CS-B 3.1-3.2	Alkyl and Carboxylate Nuc Sub Chem
	8-Sep	Lecture 3	Carboxylate Chemistry		CS-B 3.4
3	13-Sep	Lecture 4	Retrosynthesis, Route Planning		Corey Chs 1-6, handout
	15-Sep	Lecture 5	Electronic Databases and Searching the Literature	Meet in 221 BRL	Handout	Databases
4	20-Sep	Lecture 6	Aromatic Sub. Chemistry	PS 2 Due	CS-B11.1-11.2	Aromatic Sub. Chemistry
	22-Sep	Lecture 7	Transition Metal Catalyzed Cross Coupling Reactions		Heg Chs 1-2, CS-B 7.1, 8.2-8.3, 11.2-11.3	Intro to Transition Metals Metal Metiated Sub. Chem.
5	27-Sep	Lecture 8	Alcohol/Ketone Oxidations		CS-B 12.1, 12.5, 12.7	Alcohol and Ketone Oxidation
	29-Sep	Lecture 9	C=X Reductions, Protecting Groups		CS-B 5.3, 5.6, 5.7, 3.5 and handout (CK 2)	Protecting Groups C=X Bond Reductions
6	4-Oct	Lecture 10	Enolate Chemistry	PS 3 Due	CS-B 1 All	Intro to Enolate Chemistry
	6-Oct	Lecture 11	Enolate Chemistry			Enolate Stereochemistry
7	11-Oct	Lecture 12	Aldol Reactions		CS-B 2 All; (CK 4)	Aldol Reactions
	13-Oct	Lecture 11	Aldol Reactions
8	18-Oct	Lecture 12	Addition of other carbon nuc. to carbonyls		(CK 5)
	20-Oct		Midterm Exam	Midterm (Key)
9	25-Oct	Lecture 13	Alkene Synthesis and Reactivity		CS-B 2.4, 4, 5.1, 5.6 (CK 7,8,9)	Alkene Synthesis
	27-Oct	Lecture 14	Alkene Oxidation			Alkene Oxidation
10	1-Nov	Lecture 15	Alkyne Synthesis	PS 4 Due		Alkyne Synthesis
	3-Nov	Lecture 16	C=C Reductions	Outlines Due		C=C Reductions
11	8-Nov	Lecture 17	Radical Chemistry		CS-B 10.3, CS-A 11
	10-Nov	Lecture 18	Radical Chemistry
12	15-Nov	Lecture 19	Pericyclic Reactions	PS 5 Due	CS-B 6 (CK 16, 17, 18)
	17-Nov	Lecture 20	Pericyclic Reactions
13	22-Nov	Lecture 21	Pericyclic Reactions	Term Paper Due
	24-Nov	No Class	Thanksgiving
14	29-Nov	Lecture 22	Introduction to Organocatalysis	PS 6 Due
	1-Dec	Lecture 23	Strained Rings		CS-B 12.2.1, 10.2 (CK 15)	Strained Rings
	3-Dec	Saturday	Student Presentations, 9a-2p	Presentations
15	6-Dec	Lecture 24	C-H and C-C Bond Activation, time allowing		(CK 15)
Finals	TBD		FINAL EXAM	Final
CS = Carey and Sundberg; CK = Carreira and Kvaerno; Heg = Hegedus and Soderberg; () = optional reading

Problem Sets

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