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)

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
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

Lecture Notes

Handouts

Electronic Resouce Guide

Must Know pKa Table

Must Know BDE Table

Old Exams

Midterm 09
Exam
Key
Midterm 10
Exam
Key
Final 09
Exam
Key
Final 10
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