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Organic Chemistry: Principles and Mechanisms 3rd Ed - Karty
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Organic Chemistry: Principles and Mechanisms 3rd Ed - Karty
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Joel Karty
Organic Chemistry: Principles and Mechanisms 3rd Ed - Karty
ISBN: ISBN-10: 0393877655, ISBN-13: 978-0393877656
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1. "Atomic and Molecular Structure"
(9)
Molecular Formula
Lewis Structures
Electronegativity & Bond Polarity
Formal Charge
Bonding Types
Resonance Structures
IHD
Constitutional Isomers
Bond Strength
2. "Three-Dimenstional Geometry, Intermolecular Interactions, and Physical Properties"
(7)
Functional Groups
General Forces
Boiling Point
Melting Point
Solubility
Intro to Synthesis and Retrosynthesis
General Reactions
3. "Valence Bond Theory and Molecular Orbital Theory"
(3)
VSEPR Theory
Molecular Orbitals
Hybridization
4. "Isomerism 1: Conformers and Constitutional Isomers"
(12)
Nomenclature of cycloalkanes
Newman Projections
Sawhorse Projections
Converting between Newman and Sawhorse
Stability Trend of Rings
Staggered & Eclipse Conformations
Conformations of Cyclohexane
Energy Calculations of Comformations
Energy Calculations of Chair Cyclohexane
Torsional Strain
Conformational Isomers
Bicyclic Molecules
5. "Isomerism 2: Chirality, Enantiomers, and Diastereomers"
(11)
Nomenclature of Stereoisomers
Identifying Stereocenters
Diastereomers
Meso Compounds
Optical Activity
Properties of Stereoisomers
Separation Techniques
Fischer & Newman Projections
Enantiomers
Stereoisomers
Haworth Formula
6. "The Proton Transfer Reaction: An Introduction to Mechanisms, Equilibria, Free Energy Diagrams, and Charge Stability"
(11)
Equilibrium Constant and Free Energy
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
7. "An Overview of the Most Common Elementary Steps"
(19)
Stability of alkenes
Synthesis of Alkenes
Sharpless Epoxidation
Electrophilic Addition
Nucleophilic Addition
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
Substitution vs Elimination Summary
Alkyne Formation via Elimination
Rearrangement Considerations for E1
Conversion to Alcohols
Keto-Enol Tautomerism
The Hammond Postulate
8. "An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and Their Comparisons to SN2 and E2 Reactions"
(20)
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
Interpreting Energy Diagrams
Synthesis of Alkyl Halides
Sn1 Reaction and Characteristics
Sn2 Reaction and Characteristics
Intramolecular Substitution Reactions
Rearrangement Considerations for Sn1
Hydride Shift
Methyl Shift
Ring Expansion
Ring Reduction
E1 Reaction and Characteristics
E2 Reaction and Characteristics
Rearrangement Considerations for E1
9. "Competition among SN2, SN1, E2 and E1 Reactions"
(8)
Sn1 Vs Sn2 Summary Chart
E1 Vs E2 Summary Chart
E1 Vs E2 Summary Chart
Substitution vs Elimination Summary
Zaitsev Elimination
Hoffman Elimination
Zaitsev vs Hoffman Elimination
Stereochemistry and Regiochemistry of Alkene Reactions
10. "Organic Synthesis 1: Nucleophilic Substitution and Elimination Reactions and Functional Groups Transformations"
(35)
Eoxide formation from alkenes
Structure of alkenes
Cis-trans isomerism
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
Alcohol Conversion to Alkyl Halides
Electrophilic Substitution Reactions with Alcohols
Alpha Halogenation
Sharpless Epoxidation of Alkenes
Synthesis of Epoxides
Epoxidation [RCOH]
Diazonium Salts
Hofmann Elimination
Acyl Halides Conversion to Esters
Acyl Halides Conversion to Amides
Synthesis of Alkynes
Retrosynthesis - Related to Alkenes and Alkynes
11. "Organic Synthesis 2: Reactions That Alter the Carbon Skeleton, and Designing Multistep Syntheses"
(14)
Epoxide Opening Reactions
racemization
Enolate Formation
Enolate Ions
Keto-Enol Tautomerism
Alkylation of Enolates
Alpha Alkylation Reactions
Alpha Reactions
Synthesis of Keto Esters
Darzens Reaction
Alpha Reactions with Amides
Alpha Halogenation
Alpha Reactions
Haloform Reaction
12. "Electrophilic Addition to Nonpolar π Bonds 1: Addition of a Brønsted Acid"
(10)
Benzene Reactions
Carbocations and Carbanions
Stability of carbocation
Conjugate Addition
Synthesis of Dienes
Conjugate Substitution
Nomenclature of Dienes
Terpene Synthesis
Biosynthesis of Terpenes
Terpenes Reactions
13. "Electrophilic Addition to Nonpolar π Bonds 2: Reactions Involving Cyclic Transition States"
(11)
Heterocyclic Compounds
Thiol Formation
Thiol Oxidation to Disulfides
Reduction of Thioacetals to Alkanes
Halogenation of Alkynes
Hydroboration of Alkynes
Hydration of Alkynes
Oxymercuration of Alkynes
Addition of HX of Alkynes
Oxidative Cleavage of Alkynes
Reduction Reactions with Alkynes (Hydrogenation)
14. "Conjugation and Aromaticity"
(20)
Nomenclature of Aromatic Compounds
Properties of Aromatic Systems
Aromaticity
Antiaromatic and Nonaromatic
stability of conjugated system
4+2 cycloaddition
2+2 cycloaddition
1,2 and 1,4 Addition
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
Conjugate Addition
Conjugate Substitution
15. "Structure Determination 1: Mass Spectrometry"
(1)
Structure interpretation from NMR,IR,Mass spectrometry
16. "Structure Determination 2: Infrared Spectroscopy and Ultraviolet-Visible Spectroscopy"
(6)
IR Spectroscopy
The Electromagnetic Spectrum
Characteristic Absorptions in IR region
UV Theory
Absorption Trends
UV Analysis in Medicine
17. "Structure Determination 3: Nuclear Magnetic Resonance Spectroscopy"
(9)
Splitting pattren
Structure determination from NMR
NMR Theory
Magnetic Shielding
Chemical Shifts
The Number of Signals
Areas of the Peak
Spin-Spin Coupling
Chart Interpretation Trends
18. "Nucleophilic Addition to Polar π Bonds 1: Reagents That Are Strongly Nucleophilic"
(25)
Reactivity of carbonyls: aldehyde and ketones
General Reactions of Aldehyde and Ketones
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
Wittig Reaction: Alkene Formation
Grignard Addition to Aldehydes & Ketones
19. "Nucleophilic Addition to Polar π Bonds 2: Reagents That Are Weakly Nucleophilic or Non-nucleophilic, and Acid and Base Catalysis"
(39)
Aldehyde and ketone synthesis from nitrile
Enolate formation
Aldole 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
Oxidation to Carboxylic Acid
Tollens Test
Reductive Amination
Wittig Reaction: Alkene Formation
Thioacetal Formation
Cannizarro Reaction
Beckmann Rearrangement
Hydrolysis of Hemiacetals
Reductive Deoxygenation
General Reactions of Aldehyde and Ketones
General Reactions of Acetals and Hemiacetals
Pinacol Rearrangement
Aldol Addition Reaction
Retro-Aldol Reaction
Conjugate Addition
Conjugate Addition
Robinson Annulation
20. "Redox Reactions: Organometallic Reagents and Their Reactions"
(3)
Wolff-Kishner - Reduction to Alkanes
Clemmensen Reduction to Alkanes
Oxidation of Aldehydes and Ketones
21. "Organic Synthesis 3: Intermediate Topics in Synthesis Design"
(1)
Acetal Group Protecting Reactions
22. "Nucleophilic Addition-Elimination Reactions 1: Reagents That Are Strongly Nucleophilic"
(61)
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
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
23. "Nucleophilic Addition-Elimination Reactions 2: Reagents That Are Weakly Nucleophilic or Non-nuc
(9)
Synthesis of Acyl Halides
Hell-Vollhard-Zolinsky Reaction
Conversion to Tosylates, Mesylates, Triflates
Baeyer-Villiger Reaction
Claisen Condensation
Decarboxylation
Malonic Ester Synthesis
Acetoacetic Ester Synthesis
Amino Acids
24. "Aromatic Substitution 1: Electrophilic Aromatic Substitution on Benzene, and Useful Accompanying Reactions"
(17)
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
NBS Halogenation
Cycloaddition
Thermodynamic/Kinetic Product
25. "Aromatic Substitution 2: Reactions of Substituted Benzenes and Other Rings"
(18)
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
26. "The Diels-Alder Reaction, Syn Dihydroxylation, and Oxidative Cleavage"
(6)
Properties of Dienes
Stability of dienes
Synthesis of Dienes
Diels Alder
Diels Alder Reaction
Benzyne Diels Alder Reaction
27. "Reactions Involving Radicals"
(8)
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
28. "Polymers"
(3)
polymerization of alkenes
Polymerization of aldehyde
Polymerization of Dienes
29. "Biomolecules 1: An Overview of the Four Major Clases of Biomolecules"
(20)
synthesis of amines
Amino Acids
Zwitter Ions
Peptide Synthesis
General Properties of Proteins
Strecker Synthesis
lipid bilayer
Lipids in cell membrane
Steroids
Metathesis
Classification of Carbohydrates
Hydrolysis of monosacharides
Monosaccharides
Reduction of Monosaccharides
Oxidation of Monosaccharides
Enediol Rearrangement of Monosaccharides
Glycosides
Reducing vs Non Reducing Sugars
Disaccharides and Polysaccharides
terpenes
30. "Biomolecules 2: Representative Biochemical Processes Involving Biomolecules"
(11)
General Introduction
Formation of Cyclic Hemiacetal
Mutarotation
Osazone Formation
Ether and Ester Formation
Periodic Acid Reaction
Ruff Degradation
Kiliani Fischer Synthesis
Fatty acids
Synthesis of Fatty Acids
Biosynthesis of Cholesterol
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