Advanced Organic Chemistry Lectures
Lecture #13, February
Today we discuss
topics from chapter 8. We will
not be covering all of chapter
8 at this time. Todays topics are
from pages 213-22- and 225-236
and include alkyl, aryl and hydrogen
shifts; Stevens rearrangement;
Favorskii and quasi-Favorski rearrangements;
and Neber rearrangement.
Lecture #12, February
The first Midterm Test was held today. A copy of
the Midterm Exam
#1 for 2006 is now
available on the Archives page.
Lecture #11, February 7, 2006
Today we discussed some more topics from chapters 6
and 7. These included the stereochemistry of Wagner-Merwein
rearrangements, the regioselectivity of the Beckman rearrangement,
transannular hydrogen migrations and anchimeric assistance
in these systems, and the dienone-phenol rearrangement.
Lecture #10, February 5, 2006
Lecture #9, February 2, 2006
Today we had a class problem solving session where
we worked on problems from the text
book. We discussed solutions for
problems 1.1-i,j, and k; 1.2-b; 6.3-e,
f, i, n, and o; and 7.2-c. Answers can be found on the Resources page.
Lab Schedule Update. The lab missed due to the
storm day will be performed at
the end of the semester. For now, there
is no change in the lab schedule. Please return your
glassware to the kits as soon as
possible. We need this done by
Friday afternoon. Thanks.
Lecture #8, January 26, 2006
We discussed material from chapter 7. Topics included
anchimeric assistance, non-classical
cations and rearrangements of norbornyl
Lecture #7, January 24, 2006
Assignment #1 was
collected and discussed. We went
over "toolbox rules" for
carbocation rearrangements and
then explored some example rearrangements
that are observed in
organic chemistry. These include
proton and alkyl group shifts
rearrangements driven by ring
strain, pinacol and related
rearrangements (e.g. semipinacol
of protonated alpha-hydroxyketones
acid rearrangement, and dieneone-phenol
rearrangements, etc...), long
range hydrogen migrations in
large rings and migrations to
heteroatoms (e.g. the Beckman
and Baeyer-Villiger rearangements.
Lecture #6, January 19,
Today we finished
covering molecular orbitals and
introduced carbocation rearrangements.
Methods for forming carbocations
and typical carbocation reactions
were reviewed. Electronic structure
of carbocations was discussed.
Rearrangements of carbocations
was introduced with a discussion
about structures of the cations
and the transition states for
#5, January 17, 2006
Today we finish
discussion of the review assignment
and enjoy a lecture on atomic
and molecular orbitals. Molecular
orbitals are the reason that
chemistry happens. An understanding
of basic MO theory will greatly
enhance your understanding of
I made a tutorial
about molecular orbitals a few
years ago. It may prove useful
handed out. Due January 24th.
Orbital Tutorial (28
pages, 2,300 K)
#4, January 12, 2006
We discussed the
organic review assignment from
lecture 1 and the class assignment
3. The answers to the organic
review assignment are now available
to Organic Review Assignment (3 pages, 922
#3, January 10, 2006
We reviewed creation
of covalent bonds using pairs
of nucleophiles and electrophiles.
The chemistry of organometalic
reagents, enolates and related
compounds as nucleophiles were
discussed as well as carbocations,
carbonyl groups and related compounds
A handout of a
book chapter was distributed.
I can't put it on the web site
for copyright reasons so you
must get it from me before next
class if you missed it.
was set using questions from
question #1C, E, L, T, R and Y. Do question #2G, K, and
Lecture #2, January 5, 2006
We began a review
of chemistry 242 topics and discussed
resonance and basic reaction
mechanisms. The reaction toolbox
was introduced with SN1, SN2,E2,acid/base,
and addition/elimination to double
bonds were given as basic building
blocks. Generation of a carbon
nucleophile via an enolate anion
and its use with a carbon electrophile
to create a carbon-carbon bond
For next class,
review carbonyl chemistry and
nucleophilic carbon chemistry.
Specifically, review Aldol, Claissen
and Michael reactions and Grignard
and organolithium reagents.
Lecture #1, January 3, 2006
to the course. Assignment #1
was handed out and a class problem
set for discussion in lecture
2 was handed out.
Syllabus and Outline (4 pages, 160 K)
Assignment #1 (3 pages, 154 K)
Set #1 - Corrected version (1 page, 63 K)
Functional Group Conversion (5 pages, 30 K)
The lecture notes, any class handouts,
and any other lecture materials will be available here.
I try to avoid errors but my two-fingered typing techniques
often fails me late at night when I am preparing lecture
material. If there is a an error in the notes, the textbook
will have the correct information. Please let me know
of any errors so I can correct my notes on this site.
I create new lecture notes every year to avoid giving
stale lectures. As a result, lecture notes may not be
posted on the web site until after the class in question.
Please read the sections of the text pertanent to the
lecture in advance. This will greatly enhance the usefulness
of the lectures for you.