Advanced Organic Chemistry Lectures

Lecture #13, February 21, 2006

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; Sommelet-Hauser rearrangement; Favorskii and quasi-Favorski rearrangements; Ramburg-Backlund rearrangement; and Neber rearrangement.

Lecture #12, February 9, 2006

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 systems.

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 (Wagner-Meirwein rearrangements), rearrangements driven by ring strain, pinacol and related rearrangements (e.g. semipinacol rearrangement, rearrangements of protonated alpha-hydroxyketones benzylic 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, 2006

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 these migrations.

Lecture #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 this course.

I made a tutorial about molecular orbitals a few years ago. It may prove useful to you.

Assignment #1 was handed out. Due January 24th.

Molecular Orbital Tutorial (28 pages, 2,300 K)

Lecture #4, January 12, 2006

We discussed the organic review assignment from lecture 1 and the class assignment for lecture 3. The answers to the organic review assignment are now available below.

Answers to Organic Review Assignment (3 pages, 922 K)

Lecture #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 as electrophiles.

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.

An assignment was set using questions from the handout.

ASSIGNMENT: Do question #1C, E, L, T, R and Y. Do question #2G, K, and O.

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 was presented.

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

An introduction 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)

Problem 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.