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Atom and Bonding (13)
2 Subitem(s) Selected
Molecular Formula
Lewis Structures
Electronegativity & Bond Polarity
Formal Charge
Bonding Types
Resonance Structures
Carbocations and Carbanions
Molecular Orbitals
IHD
Constitutional Isomers
Hybridization
Bond Strength
VSEPR Theory
Functional Groups (10)
2 Subitem(s) Selected
Functional Groups
General Forces
Boiling Point
Melting Point
Solubility
Intro to Synthesis and Retrosynthesis
General Reactions
The Electromagnetic Spectrum
IR Spectroscopy
Characteristic Absorptions in IR region
Acids and Bases (10)
2 Subitem(s) Selected
Identification of Acid and Base
Magic Number 5.7
Factors to Determine Acid Strength
Factors to Determine Base Strength
Factor to determine base strength
Predicting the Product
Curved Arrows
pH Effects on pKa
Extraction of Organic Compounds
Radiolabeling
Alkanes (9)
2 Subitem(s) Selected
Nomenclature - General Rules
Nomenclature of Alkanes
Newman Projections
Sawhorse Projections
Converting between Newman and Sawhorse
Staggered & Eclipse Conformations
Energy Calculations of Comformations
Conformational Isomers
Torsional Strain
Cycloalkanes (5)
2 Subitem(s) Selected
Nomenclature of cycloalkanes
Stability Trend of Rings
Conformations of Cyclohexane
Energy Calculations of Chair Cyclohexane
Bicyclic Molecules
Stereochemistry (11)
2 Subitem(s) Selected
Nomenclature of Stereoisomers
Identifying Stereocenters
Diastereomers
Meso Compounds
Optical Activity
Properties of Stereoisomers
Separation Techniques
Fischer & Newman Projections
Enantiomers
Stereoisomers
Haworth Formula
Alkyl Halides: Substitution (19)
2 Subitem(s) Selected
Organo-halogen compounds
Rate of SN2 and SN1 reactions
Equilibrium Constant and Free Energy
Enthalpy and Entropy
Kinetics and the Rate Equation
Activation Energy
Transition States
The Hammond Postulate
Interpreting Energy Diagrams
Synthesis of Alkyl Halides
Sn1 Reaction and Characteristics
Sn2 Reaction and Characteristics
Sn1 Vs Sn2 Summary Chart
Intramolecular Substitution Reactions
Rearrangement Considerations for Sn1
Hydride Shift
Methyl Shift
Ring Expansion
Ring Reduction
Alkyl Halides: Elimination & Structure of Alkenes (19)
2 Subitem(s) Selected
Stability of alkenes
Synthesis of Alkenes
Sharpless Epoxidation
Electrophilic Addition
Nucleophilic Addition
Ozonolysis (Reductive/Oxidative-workup)
Properties of Alkenes
Nomenclature of Alkenes
Stereochemistry of Alkenes
E1 Reaction and Characteristics
E2 Reaction and Characteristics
E1 Vs E2 Summary Chart
Substitution vs Elimination Summary
Zaitsev vs Hoffman Elimination
Alkyne Formation via Elimination
Rearrangement Considerations for E1
Conversion to Alcohols
Hoffman Elimination
Zaitsev Elimination
Reactions of Alkenes (25)
2 Subitem(s) Selected
Epoxide formation from alkenes
Structure of alkenes
Cis-trans isomerism
polymerization of alkenes
Stability of carbocation
Stability of alkenes
Hydrohalogenation
Hydration
Halogenation
Halohydrin Formation
Addition of Alcohol
Oxymercuration
Hydroboration
Dihydroxylation
Carbene Reaction
Oxidative cleavage (Ozonolysis & KMnO4)
Hydrogenation
Rearrangements Starting with Alkenes
Free Radical Addition of HBr
Stereochemistry and Regiochemistry of Alkene Reactions
Oxidation of Alkenes
Bromination of Alkenes
Diol Formation
Simmons–Smith Reaction
Conversion to Alkenes
Alkynes (12)
2 Subitem(s) Selected
Properties of Alkynes
Acetylide Formation
Nomenclature of Alkynes
Synthesis of Alkynes
Reduction Reactions with Alkynes (Hydrogenation)
Hydration of Alkynes
Hydroboration of Alkynes
Halogenation of Alkynes
Oxymercuration of Alkynes
Addition of HX of Alkynes
Oxidative Cleavage of Alkynes
Retrosynthesis - Related to Alkenes and Alkynes
Nuclear Magnetic Resonance (NMR) (10)
2 Subitem(s) Selected
Splitting pattren
Structure interpretation from NMR,IR,Mass spectrometry
Structure determination from NMR
NMR Theory
Magnetic Shielding
Chemical Shifts
The Number of Signals
Areas of the Peak
Spin-Spin Coupling
Chart Interpretation Trends
Radical Reactions (8)
2 Subitem(s) Selected
Conversion to Alkanes
Bond Dissociation Energy
Free Radical Halogenation
Free Radical Reactions
Reactivity-Selectivity Principle
Determining the Stereochemistry of Radical Halogenation
Allylic Bromination [NBS]
Miscellaneous Radical Reactions
Alcohols, Ethers and Epoxides (29)
2 Subitem(s) Selected
Retrosynthesis - Related to Alcohols
Properties of Alcohols
Nomenclature of Alcohols
Synthesis of Alcohols
Diols
Acid & Base Properties of Alcohols
Conversion to Tosylates, Mesylates, Triflates
Alcohol Conversion to Alkyl Halides
Electrophilic Substitution Reactions with Alcohols
Pinacol Rearrangement
Inversion vs Double Inversion
Oxidation of Alcohols
Oxidative Cleavage of Vicinal Diols
Alcohol Protection
Protection as Silyl Ethers
Conversions to Alcohols
Conversion to Alkenes by Dehydration
Nomenclature of Ethers
Synthesis of Ethers
Ether Cleavage with Acid
Ether Cleavage through Sn1
Nomenclature of Epoxides
Synthesis of Epoxides
Epoxide Opening Reactions
Sharpless Epoxidation of Alkenes
Epoxidation [RCOH]
Thiol Formation
Thiol Oxidation to Disulfides
Reduction of Thioacetals to Alkanes
Organometallic Chemistry (21)
2 Subitem(s) Selected
wilkinson's catalyst
Reactions of Grignard Reagent
Grignard Formation
Reaction of Grignards with Acid [H+]
Addition of Grignards to Carbonyl Compounds
Reaction of Grignards with CO2
Formation of Organolithium Reagents
Formation of Gilman Reagents
Substitution with Gilman Reagents
Addition with Gilman Reagents
Electron Counting with Metals
General Ligand Reaction Types
Heck Reaction
Suzuki Reaction
Stille Reaction
Sonogashira Reaction
Addition of Organolithium Reagents
Addition of Organolithium Reagents to Carbonyl Compounds
Olefin Metathesis
Metathesis
General Reactions of Organometallics
Conjugated Systems (19)
2 Subitem(s) Selected
stability of conjugated system
Stability of dienes
4+2 cycloaddition
2+2 cycloaddition
Cycloaddition
Principles
1,2 and 1,4 Addition
Thermodynamic/Kinetic Product
Properties of Dienes
Nomenclature of Dienes
Synthesis of Dienes
Conjugate Addition
Conjugate Substitution
Diels Alder Reaction
Polymerization of Dienes
Diels Alder
UV Theory
Absorption Trends
UV Analysis in Medicine
Aromatic Compounds (5)
2 Subitem(s) Selected
Nomenclature of Aromatic Compounds
Properties of Aromatic Systems
Aromaticity
Antiaromatic and Nonaromatic
Heterocyclic Compounds
Reactions of Aromatic Compounds (16)
2 Subitem(s) Selected
Nitration of benzene
Halogenation
Sulfonylation [SO/HSO]
Friedel Crafts Alkylation
Friedel Crafts Acylation
Iodination
Reduction of Nitro Groups
Reduction of Benzyl Carbonyl
Side chain Halogenation
Side chain Oxidation
Electrophillic Substitution
Sulphonation
Nucleophillic Substitution
Alkylation
Benzene Reactions
NBS Halogenation
Aldehydes and Ketones (40)
2 Subitem(s) Selected
Aldehyde and ketone synthesis from nitrile
Polymerization of aldehyde
Enolate formation
Aldol condensation
Formation of acetals and hemiacetals
Reactivity of carbonyls: aldehyde and ketones
Formation of alcohols from Aldehyde and ketones
Nucleophilic addition to aldehyde and ketones
Reduction of carbonyls, aldehyde and ketones
General Characteristics of Aldehydes and Ketones
Nomenclature of Aldehydes and Ketones
Synthesis of Aldehydes and Ketones
Hydrate Formation (Gem-diols)
Nitrile Addition
Cyanohydrin Formation
Reduction of Aldehydes & Ketones
Grignard Addition to Aldehydes & Ketones
Acetal & Hemiacetals
Acetal Hydrolysis
Imine
Enamine
Imine Reactions
Stork Enamine Reaction
Wolff-Kishner - Reduction to Alkanes
Clemmensen Reduction to Alkanes
Oxidation to Carboxylic Acid
Tollens Test
Reductive Amination
Wittig Reaction: Alkene Formation
Thioacetal Formation
Cannizarro Reaction
Beckmann Rearrangement
Baeyer-Villiger Reaction
Hydrolysis of Hemiacetals
Reductive Deoxygenation
Oxidation of Aldehydes and Ketones
General Reactions of Aldehyde and Ketones
General Reactions of Acetals and Hemiacetals
Acetal Group Protecting Reactions
Pinacol Rearrangement
Carboxylic Acids and Derivatives (62)
2 Subitem(s) Selected
Properties of Carboxylic Acids
Nomenclature of Carboxylic Acids
Synthesis of Carboxylic Acids
Acid/Base Principles of COOH
Conversion to Acyl Halide
Conversion to Acid Anhydride
Conversion to Ester
Conversion to Amide
Conversion to Nitrile
Reduction of Carboxylic Acids
Fischer Esterification Reaction
Conversion to Lactones
General Reactions of Carboxylic Acid Derivates
General Reactions and Characteristics of Benzoyl Compounds
General Reactions of Carboxylic Acids
Nomenclature of Acyl Halides
Synthesis of Acyl Halides
Acyl Halides Conversion to Anhydrides
Acyl Halides Conversion to Esters
Acyl Halides Conversion to Carboxylic Acids
Acyl Halides Conversion to Amides
Acyl Halides Conversion to Ketones
Acyl Halides Conversion to Aldehydes
Curtius Rearrangement
Nucelophilic Acyl Substitution
Nomenclature of Amides
Amide Formation Using DCC
Amide Formation from Acid Halides
Amide Formation from Acid Anhydrate
Amide Formation from Nitriles
Dehydration of Amides to Nitriles
Hydrolysis of Amides
Amide Reduction (making Amines)
Hofmann Rearrangement
General Characterisitcs of Amides
General Reactions of Amides
Nomenclature of Anhydrides
Synthesis of Anhydrides
Anhydrides Conversion to Esters
Anhydrides Conversion to Carboxylic Acids
Anhydrides Conversion to Amides
Cyclic Anhydrides
Hydrolysis of Anhydride
Nomenclature of Esters
Synthesis of Esters
Reduction of Esters
Carbon Nucleophiles to Esters
Hydrolysis - Conversion Esters to Carboxylic Acid
Esters Conversion to Amide
Transesterification
Esters Addition of Grignard Reagents
Lactones
Reduction of Lactones
Ring Opening Reactions of Lactones
Conversion to Lactones
Synthesis of Nitriles
Substitution Reactions with Nitriles
Reduction to Amines [LiAlH]
Hydrolysis to Carboxylic Acids
Conversion to Aldehydes and Ketones
Reduction to Imines
Beckmann Rearrangement
Reactions of Alpha Carbon of Carbonyl (17)
2 Subitem(s) Selected
racemization
Enolate Formation
Enolate Ions
Keto-Enol Tautomerism
Alkylation of Enolates
Hell-Vollhard-Zolinsky Reaction
Decarboxylation
Alpha Alkylation Reactions
Alpha Reactions
Malonic Ester Synthesis
Acetoacetic Ester Synthesis
Synthesis of Keto Esters
Darzens Reaction
Alpha Reactions with Amides
Alpha Halogenation
Alpha Reactions
Haloform Reaction
Condensation and Conjugate Addition (9)
2 Subitem(s) Selected
Darzen Condensation
Aldol Addition Reaction
Retro-Aldol Reaction
Claisen Condensation
Dieckmann Condensation
Conjugate Addition
Conjugate Addition
Robinson Annulation
Michael Addition
Amines (22)
2 Subitem(s) Selected
Reaction of amines
synthesis of amines
Properties of Amines
Nomenclature of Amines
Synthesis - Azide Reduction
Synthesis - Gabriel Synthesis
Synthesis - Reductive Amination
Amines as Bases
Alkylation of Amines
Acylation of Amines
Hofmann Elimination
Cope Elimination
Hinsberg Test
Formation of Diazonium Salts
Diazonium Salts
Azo Coupling
Stork Enamine Reaction
Mannich Reaction
Enamine Hydrolysis
Conversion to Amines
Curtius Rearrangement
Hoffman Rearrangement
Phenol and Aryl Halides (19)
2 Subitem(s) Selected
General reaction of aryl halides
Nitration of phenol
Synthesis of phenol
Reactivity of phenol
Acidity of Phenols
Dow Process
Phenyl Ether to Phenol
Kolbe Reaction
General Reactions of Phenols
(SnAr) Addition/Elimination Reactions
(SnAr) Elimination/Addition Reactions
Diazonium Formation
Diazonium Reactions
Benzyne Reactions
Claisen Rearrangement
Claisen Rearrangement
Cope Rearrangement
Cope Rearrangement
Benzyne Diels Alder Reaction
Carbohydrates (17)
2 Subitem(s) Selected
Hydrolysis of monosacharides
Monosaccharides
General Introduction
Classification of Carbohydrates
Formation of Cyclic Hemiacetal
Mutarotation
Reduction of Monosaccharides
Oxidation of Monosaccharides
Enediol Rearrangement of Monosaccharides
Reducing vs Non Reducing Sugars
Osazone Formation
Glycosides
Ether and Ester Formation
Periodic Acid Reaction
Ruff Degradation
Kiliani Fischer Synthesis
Disaccharides and Polysaccharides
Lipids (11)
2 Subitem(s) Selected
Fatty acids
terpenes
lipid bilayer
Lipids in cell membrane
Steroids
Metathesis
Terpenes Reactions
Terpene Synthesis
Synthesis of Fatty Acids
Biosynthesis of Cholesterol
Biosynthesis of Terpenes
Amino Acids, Peptides and Protein (6)
2 Subitem(s) Selected
synthesis of amines
Amino Acids
Zwitter Ions
Peptide Synthesis
General Properties of Proteins
Strecker Synthesis
Nucleic Acids
2 Subitem(s) Selected
Biochemistry (5)
2 Subitem(s) Selected
formation of pyruvate
co-enzymes
catalysis
Co-factors
Enzymes as catalyst
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