Chem 634: Advanced Organic Chemistry— Synthesis and Reactivity

Fall 2007
Lecture Tuesdays, 7-10PM in Alison Hall

Professor Joseph M. Fox
272 Brown Labs
302-831-0191
jmfox@udel.edu

Office hours: Tuesdays, 6-7 pm; or by appointment (contact by email)
 


Textbooks:

It is not required to purchase a textbook for this course.  All required reading will be assigned as primary literature references, or will be posted as a handout.  However, those pursuing a career in organic chemistry might consider investing in one or more of the following:

• Richard Larock, Comprehensive Organic Transformations

• Jerry March, Advanced Organic Chemistry

• Greene and Wuts, Protective Groups in Organic Synthesis

• Eliel and Wilen, Stereochemistry of Organic Compounds

The textbooks above will be available on reserve in the chemistry library.


Models:
A Molecular Model Set is required.


Databases:

 
Some common chemical databases listed below. 

Beilstein Commander, accessible from computers in the chemistry library.  Alternatively, you can download the software and access the database from a campus connection on your own computer.  Note, if you complete the installation but are still unable to access the data base, make sure that the crossfire group name is "uni-del".  You do this from the Commander window: under the pulldown menu "Options", select "Change the group name".  Type "uni-del"

Web of Science is accessible through the web from any campus connection.  No software required.

SciFinder Scholar accessible from computers in the chemistry library.  Alternatively, you can download the software and access the database from a campus connection on your own computer.

Synthesis Reviews is an impressive database of references to over 16,000 reviews pertaining to organic synthesis.  The database was compiled by Prof. Philip Kocienski at Leeds.  The database can be downloaded as a textfile, but it is most useful using the EndNote biblographic management program.  A computer with the EndNote program and the Kocienski database will be made available in the Chemistry Library.
                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                           

Links and Resources

Chemical Database Searching Tutorials.  The Beilstein handouts are now out of date because of a new software interface, but the basics techniques for performing searches still apply once you get used to the new interface
 .
Handout 1: Science Citation Searching using ISI Web of Science
Handout 2:
Introduction to structure searching on Beilstein Commander
Handout 3: Introduction to substructure searching on Beilstein Commander
Handout 4: Introduction to Reaction searching with substructures on Beilstein commander
Handout 5: Introduction to Reaction searching for functional group tolerance on Beilstein commander
Handout 6: Functional Group mapping using Beilstein

Powerpoint presentations:
IR handout
Mass Spec and UV-Vis handout


Grading

There will be a midterm and a final exam (each 50% of the grade).  All exams will be open book, open notes.  Molecular models are also allowed during exams.

Weekly problem sets will be collected.

Any requests for regrades must be made in writing. 


Notecards

It is strongly recommended that everyone invest in a set of index cards to keep track of literature references for useful tranformations.  Strategies for keeping track of references will be discussed in class.


Handouts, Problem Sets, etc

Handouts/Literature References (pdf files):    1    2    3    4    5    6    7    8    9     
Handouts/Literature References (Word files):    1    2    3    4    5    6    7    8    9    

Problem Sets   :    PrePS    
1    2     3    4    5    6    7    8   
Problem Set Answers:   PrePS   1    2     3    4    5    6    7    8

OLD EXAMS
2004S Exams:    1    2    3
2004S Exam Answers:    1    2    3   

2004S Practice Exams:    1    2    3
2004S Practice Exam Answers:    1    2    3

2004F Exams: 1  2
2004F Exam Answers:  1  2

2005 Exams: 1  2
2005 Exam Answers:  1  2

2006 Exams: 1  2
2006 Exam Answers: 1  2

2007 Exams: 1  2
2007 Exam Answers: 1  2

OLD PROBLEM SETS
2004F Problem Sets   :      1  2  3  4  5  6  7
2004F Problem Set Answers:   
  1  2  3  4  5  7

2005 Problem Sets   :      1    2    3    4    5    6    7  
2005 Problem Set Answers:     1    2    3    4    5    6    7  

2006 Problem Sets   :    1    2    3    4    5    6    7  
2006 Problem Set Answers:   1    2    3    4    5    6    7   

 

Syllabus:

Problem sets will be posted each week by Thursday, and will be due on the following Tuesday.

Pre-Problem set posted

Week 1: Aug 28
Topics: Introduction to the course; C-1 homologation; organometallic coupling; 1,2 addition

Week 2: Sept 4
Topics: oxidation; C-2 homologation; enolate alkylation

Week 3: Sept 11
Topics: Claisen and Cope Rearrangements

Week 4: Sept 18

Topics:
2,3 sigmatropic rearrangements, directed reduction, directed epoxidation

Week 5: Sept 25

Topics: Reduction continued, aldol
 

Week 6
: Oct 2
Topics: ester formation.  Alkene reactions
 

Week 7: October 9
Topics: alkene preparation, alkyne preparation and reactions
Review for Exam 1

Week 8: October 16
EXAM 1

Week 9: Oct 23
Topics: Review exam, in class problem solving

Week 10: Oct 30
conjugate addition, cyclopropane formation
Group 3: in class presentations

Week 11: November 6
6 membered ring formations

Week 12: November 13
6 membered ring formations continued, Diels Alder, electrophilic aromatic substitution
 
Week 13: November 20
7 and larger rings, case studies in synthesis
 
Week 14: November 27
case studies
 
Week 15: December 4

review for final exam EXAM 2: TBA, during finals week