Second Semester Organic Chemistry Options : Bioorganic or Organic Mechanism and Synthesis

Second Semester Organic Chemistry Options:

Bioorganic or Organic Mechanism and Synthesis

Albert Matlin and Jason BelitskyDepartment 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)

Date Topic(s)

Sept. 6 Introduction, Acid-Base, Formal Charge

Sept. 8 Covalent Bonding and Hybridization

Sept. 13 Nomenclature, Alkanes and Alkenes

Sept. 15 Conformations of Alkanes/Cycloalkanes

Sept. 20 Free Radical Halogenation

Sept. 22 Stereochemistry

Sept. 29, Oct. 4 Nucleophilic Substitution, SN2, SN1

Oct. 6,11 Elimination Reactions

Oct. 13 Addition Reactions, Alkenes

Oct. 20 Addition Reactions, Conjugated -systems

 Nov. 1 Infrared and Mass Spectroscopy

Nov. 3,8 Nuclear Magnetic Resonance Spectroscopy

Nov. 10 Aromaticity

Nov. 15 Electrophilic Aromatic Substitution

Nov. 17 Reactions of Alcohols, Oxidation

Nov. 29 Carbonyl Chemistry: Ketones, Aldehydes, Grignards

Dec 1 Carbonyl Chemistry: Imines, Synthesis, Amines, AcetalsDec 6 Carboxylic Acids

Dec 8 Carboxylic Acid Derivatives

Dec 13 Enolates, Aldol Condensation

Chem 205: Principles of Organic Chemistry• ~130 students a year. Offered Spring and Fall

Topics Not Covered in Chem 205 (Partial List) EpoxidesEthers (except for EAS)ThiolsDiolsPhenols (except for EAS)Diels Alder ReactionAlkynes (except acetylide basicity and nucleophilicity)Allylic radical substitution (NBS)Polymerization 

Date Topics

February 7 Radical Reactions

February 9 Radical Polymerization

February 14 Additions Reactions to p-systems: AlkynesFebruary 16 CarbenesFebruary 21 Reduction of of p-systems

February 23 Oxidation of p-systems

March 1 Reactions of Ethers and Epoxides March 6 Synthesis March 8 p-Molecular Orbital Theory

March 13 Frontier MO theory, UV Spectroscopy

March 15,20 Pericyclic Reactions

 April 3 Electrophilic Aromatic Substitution

April 5 Reaction of Aromatic side chains and SubstituentsApril 10 Diazonium salts and Synthesis of Aromatic Compounds

April 12 Carbanions, Organometallic Reagents

April 19, 24 Enolates

May 1 Conjugate Addition and Michael ReactionsMay 3 Multi-Step Synthesis

May 8 Nucleophilic Aromatic Substitution

May 10 Benzynes

Chem 325: Organic Mechanisms and Synthesis~20 students a year. Offer in the Spring semester.

Chem 254: Bioorganic Chemistry (Jason Belitsky)~60 students a year. Offered in the Spring

semester  Week Topics 1 Class Introduction 1 Basics of Chemistry and Molecular Biology  2 Covalent / Noncovalent /Small /Large 2 Carboxyls / Esters / Amides / Amines 3 Aromatic & Heterocyclic Chemistry 3 Metals in Biology 4 Metals in Synthesis 5 Carbonyl Chemistry 5 Enolate Chemistry  6 Lipids 6 Lipid / Natural Product Biosynthesis 7 Carbohydrates 9 Peptide / Protein Synthesis 9 Protein Structure 10 Enzymatic Catalysis 11 Phosphate Esters, Nucleotides 12 Nucleic Acids 13 Biological Information Flow 13 Drug Discovery 14 Biological Probes 14 Chemical Biology

Textbook for Bioorganic Chemistry ????

Textbook for Bioorganic Chemistry ????

Bill Fuchsman has written a manuscript for his course. Email at: William.Fuchsman@Oberlin.edu 

"New" Curriculum: Chemistry Major (1994)