Spring 2004
Lecture Tuesdays and Thursdays, 4:30PM 5:45PM in 203
Brown Labs
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)
Note: This syllabus will be updated weekly— check it frequently. This is where you will get new problem sets, answer keys, handouts etc.
New Additions:
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:
By the end of this course, everyone will be expected to demonstrate
proficient use in the chemical
databases listed below. Each week there will be a question on
the problem set that requires you to follow a brief tutorial (see
below), and then to use that chemical database to conduct a simple
search.
• 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
• 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 three exams (each worth 30% of the grade). All exams will be open book, open notes. Molecular models are also allowed during exams.
Weekly problem sets will be collected and will
count for the remaining 10% of the grade.
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
Handouts/Database Searching: 1
2 3
4
5 6
Problem Sets : PrePS
1
2
3
4
5
6
7
8
Problem Set Answers: PrePS
1
2
3
4
5 6 7
Practice Exams: 1
2 3
Practice Exam Answers: 1
2 3
Exams: 1
2 3
Exam Answers: 1
2
3
Syllabus:
Week 1
Topics: Introduction to the course; C-1 homologation;
organometallic coupling; 1,2 addition
Handout/Literature references #1 (doc or pdf); Database Handout 1: Science Citation Searching using ISI Web of Science
Tuesday, Feb 10. Pre-Problem set posted
Thursday, Feb 12. Problem
set #1 posted, due
MONDAY at noon.
Week 2
Topics: oxidation; C-2 homologation; enolate alkylation
Handout/Literature references #2 (pdf
and word)
Database Handout: Handout 2: Introduction to structure searching on Beilstein Commander
Tuesday, Feb 17. Answers
to PS#1 and answers to
preproblem set
will be
reviewed at the start of class
Week 3
Topics: C-3 homologation; aldol condensation; functional groups
by nucleophilic displacement
Handout/Literature references #3 (pdf and word)
Database Handout: Handout 3: Introduction to substructure searching on Beilstein Commander
Tuesday, Feb 24. Answers to PS#2 will be reviewed at the start of class
Thursday, Feb 26. Problem
set #3 posted, due Wed at 5 pm.
Week 4
Topics: C>3 homologation; conjugate addition
No Literature references this week
Tuesday, Mar 2. Answers to PS#3 will be reviewed at the start of class
Thursday, Mar 4. Exam 1 practice questions postedWeek 5
Topics: Exam 1; Alkene preparation
Literature References #4 (pdf and doc)
Database Handout: Handout
4: Introduction to Reaction searching with substructures on Beilstein
commander
Tuesday, Mar
9. EXAM 1, open
book
Week 6
Topics: Alkene and alkyne reactions; alkyne preparation
Tuesday, Mar 16. Answers to PS#4 reviewed at
start of class
Week 7
Topics: Protecting groups; Formation of 3 and 4 membered rings
Handout/Literature references #5 (pdf and doc)
Tuesday, Mar 30.
Thursday, April 2. Problem set #5
posted, due Thursday at Noon
Week 8
Topics: Retrosynthesis; 5-membered ring
formation; stereochemical analysis
Handout/Literature references #6
Tuesday, April 6.
Thursday, April 7. Problem set #6
posted,
due Thursday at NOON
Week 9
Topics:
6-membered ring formation; aromatic subsitution; synthons
Tuesday, April 13. Answers
to PS#7 reviewed at start of class
Thursday, Apr 15. Problem set #8 posted,
due MONDAY at NOON
Week 10
Topics:
Tuesday, April 20. Answers
to PS#8 reviewed at start of class
Thursday, April 22. Problem set #9
posted, due MONDAY at NOON
Week 11
Topics:
Tuesday, April 27. Answers
to PS#9 reviewed at start of class
Thursday, April 29. Exam 2 practice questions
posted
Week 12
Topics: EXAM 2
Tuesday, May 4. EXAM 2
Thursday, May 6. Exam 2 reviewed; Problem
set #10 posted, due MONDAY
at NOON
Week 13
Topics:
Tuesday, May 11. Answers
to PS#10 reviewed at start of class
Thursday, May 13. Exam 3 practice
questions posted
Week 14
Topics:
Tuesday, May 18. Last
class
REVIEW SESSION FOR EXAM 3: TBA
EXAM 3:
TBA, during finals week