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Second Semester Organic Chemistry Options:
Bioorganic or Organic Mechanism and Synthesis
Albert Matlin and Jason Belitsky
Department of Chemistry and Biochemistry
Oberlin College, Oberlin, OH
Motivation
1.
More flexibility and choice for Chemistry majors.
2.
Introduce Biological Chemistry into the Chemistry major.
3.
Offer an Organic Chemistry course (Chem 254) that is more relevant to students
interested in biological sciences: Biochemistry, Biology, Molecular Biology,
Neuroscience and Pre-Medical.
4.
Offer a second semester Organic Chemistry course primarily for majors.
5.
Biology department reduced the chemistry requirement for their major to one
semester of organic chemistry.
"New" Curriculum: Chemistry Major (1994)
"New" Curriculum: Chemistry Major (1994)
"New" Curriculum: Chemistry Major (1994)
Chem 205: Principles of Organic Chemistry
•
~130 students a year. Offered Spring and Fall
Date
Topic(s)
Sept. 6
Sept. 8
Introduction, Acid-Base, Formal Charge
Covalent Bonding and Hybridization
Sept. 13
Sept. 15
Sept. 20
Sept. 22
Nomenclature, Alkanes and Alkenes
Conformations of Alkanes/Cycloalkanes
Free Radical Halogenation
Stereochemistry
Sept. 29, Oct. 4
Oct. 6,11
Nucleophilic Substitution, SN2, SN1
Elimination Reactions
Oct. 13
Oct. 20
Addition Reactions, Alkenes
Addition Reactions, Conjugated
Nov. 1
Nov. 3,8
Infrared and Mass Spectroscopy
Nuclear Magnetic Resonance Spectroscopy
Nov. 10
Nov. 15
Nov. 17
Aromaticity
Electrophilic Aromatic Substitution
Reactions of Alcohols, Oxidation
Nov. 29
Dec 1
Dec 6
Dec 8
Dec 13
Carbonyl Chemistry: Ketones, Aldehydes, Grignards
Carbonyl Chemistry: Imines, Synthesis, Amines, Acetals
Carboxylic Acids
Carboxylic Acid Derivatives
Enolates, Aldol Condensation
-systems
Topics Not Covered in Chem 205 (Partial List)
Epoxides
Ethers (except for EAS)
Thiols
Diols
Phenols (except for EAS)
Diels Alder Reaction
Alkynes (except acetylide basicity and nucleophilicity)
Allylic radical substitution (NBS)
Polymerization
Chem 325: Organic Mechanisms and Synthesis
~20 students a year. Offer in the Spring semester.
Date
February 7
February 9
Topics
Radical Reactions
Radical Polymerization
February 14
February 16
February 21
February 23
March 1
March 6
Additions Reactions to p-systems: Alkynes
Carbenes
Reduction of of p-systems
Oxidation of p-systems
Reactions of Ethers and Epoxides
Synthesis
March 8
March 13
March 15,20
p-Molecular Orbital Theory
Frontier MO theory, UV Spectroscopy
Pericyclic Reactions
April 3
April 5
April 10
Electrophilic Aromatic Substitution
Reaction of Aromatic side chains and Substituents
Diazonium salts and Synthesis of Aromatic Compounds
April 12
April 19, 24
May 1
May 3
Carbanions, Organometallic Reagents
Enolates
Conjugate Addition and Michael Reactions
Multi-Step Synthesis
May 8
May 10
Nucleophilic Aromatic Substitution
Benzynes
Chem 254: Bioorganic Chemistry (Jason Belitsky)
~60 students a year. Offered in the Spring semester
Week
Topics
1
1
Class Introduction
Basics of Chemistry and Molecular Biology
2
2
3
3
4
5
5
Covalent / Noncovalent /Small /Large
Carboxyls / Esters / Amides / Amines
Aromatic & Heterocyclic Chemistry
Metals in Biology
Metals in Synthesis
Carbonyl Chemistry
Enolate Chemistry
6
6
7
9
9
10
Lipids
Lipid / Natural Product Biosynthesis
Carbohydrates
Peptide / Protein Synthesis
Protein Structure
Enzymatic Catalysis
11
12
13
13
14
14
Phosphate Esters, Nucleotides
Nucleic Acids
Biological Information Flow
Drug Discovery
Biological Probes
Chemical Biology
Textbook for Bioorganic Chemistry ????
Textbook for Bioorganic Chemistry ????
Bill Fuchsman has written a manuscript for his course.
Email at: [email protected]
"New" Curriculum: Chemistry Major (1994)
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