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Organic Chemistry 8th Ed. - Brown/Iverson/Anslyn/Foote
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Organic Chemistry 8th Ed. - Brown/Iverson/Anslyn/Foote
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William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Organic Chemistry 8th Ed. - Brown/Iverson/Anslyn/Foote
ISBN: ISBN-10: 1305580354 & ISBN-13: 978-1305580350
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1. "Covalent Bonding and Shapes of Molecules"
(14)
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
2. "Alkanes and Cycloalkanes"
(13)
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
Stability Trend of Rings
Conformations of Cyclohexane
Energy Calculations of Chair Cyclohexane
Bicyclic Molecules
3. "Stereochemistry and Chirality"
(11)
Nomenclature of Stereoisomers
Identifying Stereocenters
Diastereomers
Meso Compounds
Optical Activity
Properties of Stereoisomers
Separation Techniques
Fischer & Newman Projections
Enantiomers
Stereoisomers
Haworth Formula
4. "Acids and Bases"
(8)
Magic Number 5.7
Factors to Determine Acid Strength
Factors to Determine Base Strength
Predicting the Product
Curved Arrows
pH Effects on pKa
Extraction of Organic Compounds
Radiolabeling
5. "Alkenes: Bonding, Nomenclature, and Properties"
(9)
Synthesis of Alkenes
Sharpless Epoxidation
Electrophilic Addition
Nucleophilic Addition
Ozonolysis (Reductive/Oxidative-workup)
Properties of Alkenes
Nomenclature of Alkenes
Stereochemistry of Alkenes
Conversion to Alcohols
6. "Reactions of Alkenes"
(16)
Hydration
Halohydrin Formation
Addition of Alcohol
Oxymercuration
Hydroboration
Dihydroxylation
Carbene Reaction
Oxidative cleavage (Ozonolysis & KMnO4)
Hydrogenation
Rearrangements Starting with Alkenes
Stereochemistry and Regiochemistry of Alkene Reactions
Oxidation of Alkenes
Bromination of Alkenes
Diol Formation
Simmons–Smith Reaction
Conversion to Alkenes
7. "Alkynes"
(12)
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
8. "Haloalkanes, Halogenation, and Radical Reactions"
(11)
Hydrohalogenation
Halogenation
Conversion to Alkanes
Bond Dissociation Energy
Free Radical Halogenation
Free Radical Addition of HBr
Free Radical Reactions
Reactivity-Selectivity Principle
Determining the Stereochemsitry of Radical Halogenation
Allylic Bromination [NBS]
Miscellaneous Radical Reactions
9. "Nucleophilic Substitution and β-Elimination"
(26)
Substitution vs Elimination Summary
E1 Reaction and Characteristics
E2 Reaction and Characteristics
Equilibrium Constant and Free Energy
E1 Vs E2 Summary Chart
Rearrangement Considerations for E1
Zaitsev vs Hoffman Elimination
Alkyne Formation via Elimination
Hoffman Elimination
Zaitsev Elimination
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
10. "Alcohols"
(14)
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
11. "Ethers, Epoxides, and Sulfides"
(15)
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
12. "Infrared Spectroscopy"
(9)
Functional Groups
General Forces
Boiling Point
Melting Point
Solubility
Intro to Synthesis and Retrosynthesis
General Reactions
IR Spectroscopy
Characteristic Absorptions in IR region
13. "Nuclear Magnetic Resonance Spectroscopy"
(7)
NMR Theory
Magnetic Shielding
Chemical Shifts
The Number of Signals
Areas of the Peak
Spin-Spin Coupling
Chart Interpretation Trends
14. "Mass Spectrometry"
(1)
The Electromagnetic Spectrum
15. "An Introduction to Organometallic Compounds"
(12)
Grignard Formation
Reaction of Grignards with Acid [H+]
Addition of Grignards to Carbonyl Compounds
Reaction of Grignards with CO2
Formation of Gilman Reagents
Substitution with Gilman Reagents
Addition with Gilman Reagents
Electron Counting with Metals
Suzuki Reaction
Stille Reaction
Sonogashira Reaction
Addition of Organolithium Reagents to Carbonyl Compounds
16. "Aldehydes and Ketones"
(30)
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
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
17. "Carboxylic Acids"
(13)
Properties of Carboxylic Acids
Nomenclature of Carboxylic Acids
Synthesis of Carboxylic Acids
Acid/Base Principles of COOH
General Reactions of Carboxylic Acids
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
18. "Functional Derivatives of Carboxylic Acids"
(49)
General Reactions of Carboxylic Acid Derivates
General Reactions and Characteristics of Benzoyl Compounds
Nomenclature of Acyl Halides
Synthesis of 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
19. "Enolate Anions and Enamines"
(24)
Aldol Addition Reaction
Retro-Aldol Reaction
Claisen Condensation
Dieckmann Condensation
Conjugate Addition
Conjugate Addition
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
Enamine
Michael Addition
20. "Dienes, Conjugated Systems, and Pericyclic Reactions"
(13)
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
Diels Alder
UV Theory
Absorption Trends
UV Analysis in Medicine
21. "Benzene and the Concept of Aromaticity"
(12)
Nomenclature of Aromatic Compounds
Properties of Aromatic Systems
Aromaticity
Antiaromatic and Nonaromatic
Heterocyclic Compounds
Reduction of Benzyl Carbonyl
Benzene Reactions
Acidity of Phenols
Phenyl Ether to Phenol
General Reactions of Phenols
Benzyne Reactions
Benzyne Diels Alder Reaction
22. "Reactions of Benzene and Its Derivatives"
(29)
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
Friedel Crafts Alkylation
Friedel Crafts Acylation
Electrophillic Substitution
Nucleophillic Substitution
Reduction of Nitro Groups
Nitration
Halogenation
Sulfonylation [SO/HSO]
Iodination
Side chain Halogenation
Side chain Oxidation
Sulphonation
Alkylation
NBS Halogenation
23. "Amines"
(20)
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
24. "Catalytic Carbon-Carbon Bond Formation"
(7)
Formation of Organolithium Reagents
General Ligand Reaction Types
General Reactions of Organometallics
Addition of Organolithium Reagents
Heck Reaction
Olefin Metathesis
Metathesis
25. "Carbohydrates"
(15)
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
26. "Lipids"
(7)
Steroids
Metathesis
Terpenes Reactions
Terpene Synthesis
Synthesis of Fatty Acids
Biosynthesis of Cholesterol
Biosynthesis of Terpenes
27. "Amino Acids and Proteins"
(5)
Amino Acids
Zwitter Ions
Peptide Synthesis
General Properties of Proteins
Strecker Synthesis
28. "Nucleic Acids"
(1)
Robinson Annulation
29. "Organic Polymer Chemistry"
(1)
Polymerization of Dienes
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