Organic Chemistry I

Allylic and Benzylic Radicals, NBS, Retrosynthesis

Radical Reactions, Halogenation of Alkanes, Radical Stability, Radical Addition to Alkenes

Gilman Reagents, Heck Reaction, Stille Reaction, Suziki Reaction

Amine Reactions, Ether Cleavage, Epoxide Ring Opening

Alcohol Reactions, HX, SOCl2, PBr3, Sulfonate Esters, Dehydrations, Oxidation

Williamson Ether Synthesis, Consecutive E2 Eliminations, Substitutions vs Eliminations

E1, Stereochemistry of E2 and E1, E1 vs E2, SN2 vs E2, SN1 vs E1

Intermolecular vs. Intramolecular, Eliminations, E2, Zaitsev’s Rule,

SN1 Mechanism: Stereochemistry, Leaving Group, Solvent Effect, Temperature; SN1 vs. SN2

SN2 Mechanism: Nucleophiles, Leaving Groups, Solvent Effects; SN1 Mechanism

Diels-Alder Reaction: Diene Stereochemistry, Endo; Substitution and Elimination, SN2 Mechanism, SN1 Mechanism

Thermodynamic and Kinetic control of 1,2- and 1,4-additions, Diels-Alder Reactions, Regioselectivity, Stereoselective

Stability of Dienes, Molecular Orbital of alkenes and dienes, Allylic and Benzylic Carbocation, 1,2 and 1,4-addition

Acetylide Formation, Acetylide Reaction, Synthesis, Retrosynthesis

Hydration Terminal Alkyne, Hydroboration-Oxidation, Addition of Halides, Addition of Hydrogen, Poisoned Catalyst, Dissolving Metal Reduction

Stereochemistry of Electrophilic Addition reactions to Alkenes, N and P asymmetric centers

Diastereomers, Meso Compounds, Reactions of compounds with Assymetric Centers

R and S nomenclature, Fisher Projections, Optical Activity, Enantiomeric Excess

Stereochemistry, Chirality, Assymetric Centers, Stereocenters, Fischer Projections, R and S

Hydroboration Oxidation, Catalytic Hydrogenation, Alkene Stability

Halogenation, Oxymercuration- Reduction, Addition of Peroxy acid

Addition of Alcohols, Carbocation Rearrangement, Addition of Halogens, Formation of Halohydrin

Reactions of Alkenes, Hydrohalogenations, Carbocation Stability, Regioselectivity, Markovnikov’s Rule, Addition of Water

Thermodynamics, Kinetics, Nucleophiles and Electrophiles

E and Z nomenclature, Thermodynamics and Kinetics, Keq, ∆G

Degree of Unsaturation, Nomenclature of Alkenes, Cis and Trans, E and Z

Conformations, Ring Strain, Chair Conformations, Disubstituted Cyclohexane Conformations

Conformations of Ethane and Butane

Nomenclature: Cycloalkanes, Alkyl Halides, Ether, Alcohols, Amines

Alkane Nomenclature, Common Side Group Names

Resonance, Inductive Effects, Lewis Acids and Bases, Nomenclature

Products of Acid and Base Reactions, pKa’s by Functional Group, Acidity by Structure,

Hybridization: Sp, Acids and Bases, pKa, Acid and Bases Mechanisms

Covalent Bonds, Polar Covalent Bonds, Lewis Structures, Formal Charge, skeletal structrue

Atomic Structure, Atomic Orbitals, Valance Electrons, Ionic Bond

Radical Reactions, Halogenation of Alkanes, Relative Selectivity, Radical Addition to Alkenes, Benzylic/Allylic Bromonation, Stereochemistry

Williamson Ether Synthesis, Consecutive E2 Eliminations, Addition of HX to Alcohol, Conversion of Alcohols to Halides (PBr3, SOCl2), Sulfonate Ester

Substitution and Elimination Competition, Intramolecular Substitutions, E1 and E2 stereochemistry,

SN1, E2, E1

Substitutions and Eliminations, SN2, Substrates, Nucleophiles, Leaving Groups, Solvents

REduction of Alkynes, Acetylide Synthesis, Retrosynthesis, Dienes, MO

Diastereomers, Meso Compounds, Stereoselectivity,

R,S Nomenclature, Optical Rotation

Addition of Hydrogen, Alkene Stability, Stereochemistry, Asymmetric Centers, Chiral

Oxymercuration-reduction, Alkoxymercuration-reduction, Addition of Halogen, Hydroboration-oxidation, Epoxidation

Reactions of Alkenes, Addition of Hydrogen Halides, Carbocation rearrangements, Addition of Water

Enhancing Learning in a Large Enrollment Courses: Podcasts, Wiki, & Lab CurriculumDr. Mark MorvantUniversity of Oklahoma

Nomenclature Part 2, Physical Properties

Nomenclature Part 1