Lecture Tuesdays 7PM–10PM 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:
• Carey and Sundberg, Advanced Organic Chemistry
B
• 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
All exams will be open
book, open notes. The midterm will count for 30% of the total
grade, and the final exam will count for 50% of the final grade.
Collected assignments will count toward the remaining 20%.
Molecular models are also allowed during exams.
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
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 and Exams
Problem Sets : PrePS
1 2 3 4 5 6 7
Problem Set Answers: PrePS 1 2 3 4 5 7
Exams: 1 2
Exam Answers: 1 2
Syllabus:
Problem sets will be posted each
week by Thursday, and will be due on the following Tuesday.
Week 1: August 31
Topics: Introduction to the course; C-1 homologation;
organometallic coupling; 1,2 addition
Pre-Problem set
posted
Week 2: Sept 7
Topics: oxidation; C-2 homologation; enolate alkylation
Problem set 1
Week 3: Sept 14
Topics: Claisen and Cope Rearrangements
Problem set 2
Week 4: Sept 21
Topics: 2,3 sigmatropic rearrangements,
directed reduction, directed epoxidation
Problem set 3
Week 5: Sept
28
Topics: Reduction continued, aldol
Problem set 4
Week 6: October 5
Topics: ester formation.
Alkene reactions
Review for exam 1
Week 7: October 12
Exam 1
Week 8: October 19
Topics: alkene preparation, alkyne preparation and reactions
Problem set 6
Week 9: October 26
Topics: conjugate addition, cyclopropane formation
Problem set 7
November 2
NO Class this week-- election day
Week 10: November 9
6 membered ring formations
Week 11: November 16
6 membered ring formations, Diels
Alder, electrophilic aromatic substitution
Week 12: November 23
7 and larger rings, case studies in synthesis
Week 13: November 30
case studies
Week 14: December 7
EXAM
2:
TBA, during finals week