CHE-251
Organic Chemistry II
Fall 2005
Gustavus Adolphus College
Prof. Scott Bur
Office: 303B, Nobel Hall
Telephone: 933-7038
Email: sbur@gustavus.edu
Textbook: Organic Chemistry, Brown, Foote, and Iverson; 4th edition (2005)
Supplies : Molecular models. These are not a requirement, but I strongly urge you to purchase a set. You may use the model sets during the exams.
Classroom: Wallenburg auditorium, Nobel Hall
Office Hours: My scheduled office hours are the following, or by appointment;
Wednesday and Thursday 11:30 - 12:30
Homework:
I will give you a selection of homework problems out of the textbook to do as we cover each topic in class. You should try to work the assigned problems on a regular basis, rather than trying to do them all right before the exam. Any questions that you have with regard to the homework problems are welcome as topics for discussion during or outside of class. These homework problems will not be collected for a grade. As the exams will reflect the concepts and skills that the homework will develop, however, your grades will ultimately reflect your performance on these homework problems.
Because chemistry is a collaborative science, you will also be assigned four group homework assignments throughout the semester. These homework assignments will be collected for a grade. Your cumulative grade on the homework assignments may be used to 'replace' your worst test grade if it is to your advantage. I will assign the groups (4-5 people) and distribute the homework assignments one-week before they are due. One person in each group will be required to contact the other group members to arrange meeting times and one set of homework will be turned in, with all of your names, for credit. The group homework assignments will be due on September 16th, October 14th, November 11th, December 2nd.
Course Coverage
In second semester organic chemistry, we will study the chemistry of the carbonyl and amine functional groups, aromatics, and conjugated systems. Not unlike first semester, we will primarily be focused on reaction mechanisms. However, since we will become familiar with a broad spectrum of reactions, we will also expand our attention to include organic synthesis. We will learn how to plan the synthesis of complex organic compounds from more simple compounds and to use spectroscopic and other data to determine structures.
The schedule below gives an outline of the topics we will study, including the textbook chapter and a tentative class schedule. Note that this in VERY tentative, if we need to spend more time on a subject, we will.
|
Topic
|
Reading
|
Lectures
|
|
Spectroscopy Review
|
Chapters 12 & 13
|
Sept 7, 8, 9
|
|
Review of Infrared and NMR Spectroscopy
Interpreting DEPT and Hetcor Experiments
Solving Structures from IR and NMR Spectra
|
|
Ethers, Sulfides, and Epoxides
|
Chapter 11
|
Sept 12, 14, 15, 16
|
|
Structure and Nomenclature
Physical Properties
Preparation of Ethers
Williamson Ether Synthesis
Acid Catalyzed Dimerization of Alcohols
Reactions of Ethers
Protecting Groups
Epoxides
Crown Ethers
Thioethers
|
|
Alkynes
|
Chapter 6
|
Sept 19, 21, 22, 26
|
|
Review of Alkene Reactions
Structure and Nomenclature of Alkynes
Physical Properties of Alkynes
Acid Base Chemistry of Alkynes
Preparation of Alkynes
Double Elimination
Alkylation of Acetylene
Reactions of Alkynes
Electrophilic Additions
Hydroboration / Oxidation
Oxymercuration
Reduction of Alkynes
Retrosynthetic Analysis
|
|
Organometalics
|
Chapter 15 (and 24)
|
Sept 29, 30; Oct 3, 5, 6
|
|
Grignard and Organolithium Formation and Reactivity
Lithium Diorganocopper Reagents
Carbenes
Organopalladium Reactiosn (Heck)
Olefin Metathesis
|
|
Aldehydes and Ketones
|
Chapter 16
|
Oct 7, 10, 12, 13, 14
|
|
Structure and Bonding
Nomenclature
Physical Properties
Reactions
Addition of Carbon Nucleophiles
Addition of Oxygen Nucleophiles
Equilibrium Reactions and How to Drive Unfavorable Equilibria
Addition of Nitrogen Nucleophiles
Keto-Enol Tautomerism.
Oxidation
Reduction
Haloform Reaction
|
|
Carboxylic Acids
Carboxylic Acid Derivatives
|
Chapter 17
Chapter 18
|
Oct 17, 19
Oct 20, 26, 27, 28, 31
Nov 2
|
|
Structure and Nomenclature Of Carboxylic Acids
Physical Properties of Carboxylic Acids
Acid - Base Chemistry of Carboxylic Acids
Preparation of Carboxylic Acids
Reactions of Carboxylic Acids
Reduction of Carboxylic Acids
Esterification
Acid Chlorides
Decarboxylation of b-Keto Esters
Characteristic Reactions of Carboxylic Acid Derivatives
Hydrolysis
Reactions with Oxygen, Nitrogen, and Carbon Nucleophiles
Reduction
|
|
Mass Spectometry
|
Chapter 14
|
Nov 3, 4
|
|
Workings of a Mass Spectrometer
Interpreting Mass Spectra
Using Mass Specta to Identify Unknown Molecules
|
|
Enolates and Enamines
|
Chapter 19
|
Nov 7, 9, 10, 11, 14
|
|
Formation of Enolates
Aldol Reaction
Claisen and Diekmann Condensations
Enamines
Acetoacetic Ester and Malonic Ester Synthesis
Conjugate Addition
Kinetic vs Thermodynamic Control
|
|
Benzene and Aromaticity
|
Chapter 21
|
Nov 16, 17, 21
|
|
Structure of Benzene (Kekulé Structures)
Concept of Aromaticity
Nomenclature
Phenols
Reactions at the Benzylic Position
|
|
Benzene and derivatives
|
Chapter 22
|
Nov 23, 28, 30; Dec 1, 2
|
|
Electrophilic Aromatic Substitution
Nucleophilic Substitution
|
|
Amines
|
Chapter 23
|
Dec 5, 7, 8
|
|
Structure and Nomenclature
Chirality of Amines and Quaternary Ammonium
Physical Properties
Acid-Base Chemistry
Preparation
Reactions
Nitrous Acid
Hofmann Elimination
Cope Elimination
|
|
Synthesis
|
Chapter 20, 24
|
Dec 12, 14
|
|
Conjugated Dienes
Diels-Alder Reaction
Pericyclic Reactions
|
Laboratory
We will use the following text books:
Modern Projects and Experiments in Organic Chemistry: Miniscale and Standard Taper Microscale, Mohrig et al. (2003).
Techniques in Organic Chemistry, Mohrig et al. (2003).
Course Pack
|
Experiment
|
Lab Dates
|
Lab
|
|
1
|
9/12 - 9/22
|
Isolation of essential oils
Goal: Isolate the essential oil from caraway or cumin seeds. Identify the major component using NMR spectroscopy.
|
|
2
|
10/3 - 10/20
|
Grignard Synthesis of an Alcohol
Goal: Synthesize an alcohol from a Grignard reagent and an aldehyde or ketone. The Grignard reagent is synthesized by conversion of an alcohol to an alkyl halide followed by reaction of the alkyl halide with magnesium.
|
|
3
|
10/26 - 11/15
|
Hydrogenation I
Goal: Determine the products from catalytic hydrogenation of cinnamic acid derivatives. Explore functional group compatibility under palladium catalysis conditions.
|
|
4
|
11/16 - 11/22
|
Aromatic Substitution
Goal: Predict the regiochemistry of electrophilic aromatic substitution reactions using computational tools. Identify the product from the bromination of acetanalide derivatives and compare with the predicted outcome.
|
|
5
|
11/28 - 12/1
|
Dilantin Synthesis
Goal: Synthesize the anti-seizure drug Dilantin from benzyl and urea. Determine the mechanism of the benzilic rearrangement to produces Dilantin.
|
|
|
12/5 - 12/8
|
Check out
|