Chem 634 - Advanced Organic Chemistry - Synthesis and Reactivity

University of Delaware, Fall 2013

Prof. Donald A. Watson

dawatson-at-udel.edu

Lecture: Tuesday and Thursday 2-3:15p, Brown Lab (BRL) 116

Office hour: 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.
Classics in Stereoselective Synthesis, Erick M. Carreira, Lisbet Kvaerno

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.

The Logic of Chemical Synthesis, Corey, E. J.; Cheng, X.

Topics (Approximate Schedule)

Week

Date

Lecture

Topic

Notes

Reading

1

Aug 27

Lecture 1

Introduction, Arrow Pushing, Mechanism

 

 Corey Chs 1-6, handout

 

Aug 29

Lecture 2

Retrosynthesis, Route Planning

 

 

2

Sept 3

Lecture 3

Nuc. Substitution Chemistry

PS 1 Due

CS-B 3.1-3.2

 

Sept 5

Lecture 4

Carboxylate Chemistry

 

CS-B 3.4

3

Sept 10

Lecture 6

Electronic Databases and Searching the Literature

Meet in 221 BRL

Handout

 

Sept 12

Lecture 5

Protecting Groups

 

 

4

Sept 17

Lecture 7

Aromatic Sub. Chemistry

 

CS-B11.1-11.2

 

Sept 19

Lecture 8

Classic Organometallics and Intro to TM Organometallics

 

Heg Chs 1-2, CS-B 7.1, 8.2-8.3, 11.2-11.3

5

Sept 24

Lecture 9

Transition Metal Cat. Cross Coupling Reactions

PS 2 Due

 

 

Sept 26

Lecture 10

Alcohol/Ketone Oxidations

 

CS-B 12.1, 12.5, 12.7

6

Oct 1

Lecture 11

C=X Reductions

 

CS-B 5.3, 5.6, 5.7, 3.5 (CK 2)

 

Oct 3

Lecture 12

Enolate Chemistry

 

CS-B 1 All

7

Oct 8

Lecture 11

Enolate Chemistry

 

 

 

Oct 10

Lecture 12

Aldol Reactions

PS 3 Due

CS-B 2 All; (CK 4)

8

Oct 15

 

Midterm Exam

Midterm

 

 

Oct 17

Lecture 13

Aldol Reactions

 

 

9

Oct 22

Lecture 14

Addition of other carbon nuc. to carbonyls

Outlines Due

(CK 5)

 

Oct 24

Lecture 15

Alkene Synthesis and Reactivity

 

CS-B 2.4, 4, 5.1, 5.6 (CK 7,8,9)

10

Oct 29

Lecture 16

Alkene Synthesis and Reactivity

 

 

 

Oct 31

Lecture 17

Alkene Oxidation

PS 4 Due

 

11

Nov 5

Lecture 18

Alkyne Synthesis

 

 

 

Nov 7

Lecture 19

C=C Reductions

 

 

12

Nov 12

Lecture 20

Radical Chemistry

 

CS-B 10.3, CS-A 11

 

Nov 14

Lecture 21

Radical Chemistry

PS 5 Due

 

13

Nov 19

Lecture 22

Pericyclic Reactions

 

CS-B 6 (CK 16, 17, 18)

 

Nov 21

Lecture 23

Pericyclic Reactions

 

 

 

Nov 23

Saturday

Student Presentations, 9a-2p

Presentations

BRL 220

14

Nov 26

Lecture 24

Introduction to Organocatalysis

 

 

 

Nov 28

No Class

Thanksgiving

 

 

15

Dec 3

Lecture 25

Strained Rings

Term Paper & PS 6 Due

CS-B 12.2.1, 10.2 (CK 15)

Finals

TBD

 

FINAL EXAM

Final

 

 

Problem Sets

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

Final Exam

 

 

 

Handouts

Electronic Resouce Guide

Must Know pKa Table

Must Know BDE Table

Old Exams

Midterm 09
Exam
Key
Midterm 10
Exam
Key
Midterm 11 Exam Key
Midterm 12 Exam Key
Midterm 13 Exam Key
Final 09
Exam
Key
Final 10
Exam
Key
Final 11 Exam Key
Final 12 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