Organic Chemistry 1 & 2 - Notes

Orgo 1 - Notes

Formal Charge

Constitutional Isomers (aka Structural Isomers)

Resonance Structures

Bond Angles & Molecular Shape

Condensed, Partially Condensed & Lewis Structures

Functional Groups (Alcohols; Ethers; Amines; Aldehydes; Ketones; Carboxylic Acids; Anhydrides; Esters; Amides)

Organic Compound Classifications (primary; secondary; tertiary; quaternary)

Intermolecular Forces (Hydrogen Bonding; Vander Waals Forces)

Nomenclature & IUPAC System (Alkanes; Cycloalkanes)

Newman Projections

Cyclohexane Chair Conformations (equatorial vs axial energy levels & stabilization)

Stereoisomers, Enantiomers (including Enantiomer Nomenclature) & identifying Diastereomers, Chiral Centers (Chirality) and R&S Assignment, cis vs trans & identifying Meso Compounds

Acids & Bases (identifying the conjugate acid & conjugate base); Acid Strength (Inductive Effect; Resonance Effect); Equilibrium favors formation of...

E1, E2, SN1, SN2 Reactions

Bond Breaking (Homolitic & Heterolitic cleavage - Homolysis & Heterolysis)

Bond Dissociation Energy (BDE) (Activation Energy; Endothermic & Exothermic Reactions)

Preparation of Haloalkanes by Halogenation of Alkanes (Br or Cl)

Monochlorination (Halogenation)

Radical Halogenation (Initiation, Propagation #1, Propagation #2, Termination)

Energetics of Chain Propagation

Preparation of Haloalkanes by Halogenation of Alkanes

Halogenation (Bromination vs Chlorination)

Organometallic Reagents

Preparation of Alcohols, Ethers, and Epoxides

Preparation of Alkoxides & Forming Epoxides from Halohydrins

Dehydration of Alcohols to Alkenes

Carbocation Rearrangements

Conversion of Alcohols to Alkyl Halides with HX

Conversion of Alcohols to Alkyl Halides with SOCl2 & PBr3

Conversion of Alcohols to Alkyl Tosylates

Epoxide Reactions with Acids

Opening Epoxide Ring with Strong Nucleophile

Hydrohalogenation - Ionic & Electrophilic Addition of HX

Hydration - Electrophilic Addition of Water

Halogenation (Anti Addition)

Halogenation - Electrophilic Addition

Halohydrin Formation (Anti Addition)

Hydroboration-Oxidation (SYN Addition)

Hydroboration-Oxidation vs Hydration

Radical Addition of HBR

Catalytic Hydrogenation (SYN Addition)

Epoxidation (Oxidation Reaction)

Dihydroxylation (Oxidation Reaction)

Oxidative Cleavage (Oxidation Reaction)

Lewis Acids & Bases

Grignard Reagents

Organometallic Reagents

Coupling Reactions of Organocuprates

Organocuprates

Alkyl Halide Nomenclature

SN2 Reactions (Nucleophilic Substitution)

SN1 Reactions (Nucleophilic Substitution)

Carbocation Stability

Determining SN1 or SN2 based on Alkyl Halide Class & Strong/Weak Nucleophile

SN1 & SN2 Stereochemistry




Orgo 2 - Notes


Preparation of Alkynes

Alkyne Rxns - Bases that can Deprotonate Acetylene

Keto-Enol Tautomerization

Hydroboration-Oxidation

Keto-Enol Tautomerization & Hydroboration-Oxidation

Acetylide Anion Rxns

Alkyne Nomenclature

Conjugate Dienes

Electron Delocalization & Hybridization

Stability of Conjugate Dienes

Diels-Alder Rxn (Rules 1-4)

Nomenclature of Benzene Derivatives

Stability of Benzene

Classifying Aromatic Heterocycles

Ionic Aromatic Compounds & Heterocycle Hybridization

Halogenation

Substituent Effects on Electrophilic Aromatic Substitution

Orientation Effects of Substituted Benzenes

Rxns of Activated Rings

Nucleophilic Aromatic Substitution - Addition-Elimination

Nucleophilic Aromatic Substitution - Elimination-Addition

Oxidation of Alcohol

Carbonyl Reduction

Protecting Groups

Organocuprates (Gilman Reagents)

Simmons-Smith Rxn

Nucleophilic Addition of Hydride

Suzuki Mechanism

Heck Rxn

Mass Spectrometry

IR Structure

Proton NMR

Imine Formation

Acetal Formation

Acetal Hydrolysis

Preparation of Carboxylic Acids

Acid-Base Rxns of Carboxylic Acids

Carboxylic Acid Inductive Effects

Substituted Benzoic Acids

Properties of Carboxylic Acid Derivatives

Acid Chloride Nomenclature

Nucleophilic Acyl Substitution

Amide Synthesis

Anhydride Rxn

Carboxylic Acid - Fischer Esterification

Nitrile Formation

Hydrolysis (Amide Hydrolysis in Acid, Ester-Acid Hydrolysis, Ester-Base Hydrolysis)

Esters - Lactone (Cyclic Ester)

Hydrolysis of Acetals

Carboxylic Acid - Acid Base Rxns

Nomenclature of Carboxylic Acid Derivatives

Fischer Esterification - Carboxylic Acid

Enolate

Halogenation at Alpha Carbon

Haloform Rxn

Direct Enolate Alkylation

Aldol Rxn

Claisen Rxn

Malonic Ester Rxn

Acetoacetic Ester Rxn

Michael Rxn