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Organic Chemistry, 5th Ed. Maitland Jones & Steven Fleming
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Organic Chemistry, 5th Ed. Maitland Jones & Steven Fleming
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Maitland Jones & Steven Fleming
Organic Chemistry, 5th Ed. Maitland Jones & Steven Fleming
ISBN: ISBN-10: 0393124231 & ISBN-13: 978-0393124231
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1. "Atoms and Molecules; Orbitals and Bonding"
(13)
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
2. "Alkanes"
(9)
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
3. "Alkenes and Alkynes"
(23)
Equilibrium Constant and Free Energy
Enthalpy and Entropy
Kinetics and the Rate Equation
Activation Energy
Transition States
The Hammond Postulate
Interpreting Energy Diagrams
Properties of Alkenes
Nomenclature of Alkenes
Stereochemistry of Alkenes
Synthesis of Alkenes
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
4. "Stereochemistry"
(11)
Nomenclature of Stereoisomers
Identifying Stereocenters
Diastereomers
Meso Compounds
Optical Activity
Properties of Stereoisomers
Separation Techniques
Fischer & Newman Projections
Enantiomers
Stereoisomers
Haworth Formula
5. "Rings"
(4)
Stability Trend of Rings
Conformations of Cyclohexane
Energy Calculations of Chair Cyclohexane
Bicyclic Molecules
6. "Substituted Alkanes: Alkyl Halides, Alcohols, Amines, Ethers, Thiols, and Thioesters"
(27)
Synthesis of Alkyl Halides
Properties of Alcohols
Nomenclature 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
Thiol Formation
Reduction of Thioacetals to Alkanes
Intramolecular Substitution Reactions
7. "Substitution Reactions: The SN2 and SN1 Reactions"
(8)
Sn1 Reaction and Characteristics
Sn2 Reaction and Characteristics
Sn1 Vs Sn2 Summary Chart
Rearrangement Considerations for Sn1
Hydride Shift
Methyl Shift
Ring Expansion
Ring Reduction
8. "Elimination Reactions: The E1 and E2 Reactions"
(18)
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
9. "Analytical Chemistry: Spectroscopy"
(13)
UV Theory
Absorption Trends
UV Analysis in Medicine
The Electromagnetic Spectrum
IR Spectroscopy
Characteristic Absorptions in IR region
NMR Theory
Magnetic Shielding
Chemical Shifts
The Number of Signals
Areas of the Peak
Spin-Spin Coupling
Chart Interpretation Trends
10. "Electrophilic Additions to Alkenes"
(12)
Halohydrin Formation
Addition of Alcohol
Dihydroxylation
Carbene Reaction
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
11. "More Additions to π Bonds"
(8)
Halogenation
Oxymercuration
Epoxidation [RCOH]
Oxidative cleavage (Ozonolysis & KMnO4)
Hydrohalogenation
Hydration
Hydroboration
Hydrogenation
12. "Radical Reactions"
(8)
Conversion to Alkanes
Bond Dissociation Energy
Free Radical Halogenation
Free Radical Reactions
Reactivity-Selectivity Principle
Determining the Stereochemsitry of Radical Halogenation
Allylic Bromination [NBS]
Miscellaneous Radical Reactions
13. "Dienes and the Allyl System: 2p Orbitals in Conjugation"
(14)
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
14. "Aromaticity"
(5)
Nomenclature of Aromatic Compounds
Properties of Aromatic Systems
Aromaticity
Antiaromatic and Nonaromatic
Heterocyclic Compounds
15. "Substitution Reactions of Aromatic Compounds"
(16)
Nitration
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
16. "Carbonyl Chemistry 1: Addition Reactions"
(12)
Synthesis of Alcohols
Imine
Enamine
Imine Reactions
Stork Enamine Reaction
Formation of Organolithium Reagents
Addition of Organolithium Reagents to Carbonyl Compounds
Addition of Organolithium Reagents
General Reactions of Organometallics
Retrosynthesis - Related to Alcohols
Thiol Oxidation to Disulfides
Wittig Reaction: Alkene Formation
17. "Carboxylic Acids"
(14)
Properties of Carboxylic Acids
Nomenclature of Carboxylic Acids
Synthesis of Carboxylic Acids
Acid/Base Principles of COOH
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
18. "Derivatives of Carboxylic Acids: Acyl Compounds"
(48)
Conversion to Acyl Halide
Nomenclature of Acyl Halides
Synthesis of of Acyl Halides
Acyl Halides Conversion to Esters
Acyl Halides Conversion to Anhydrides
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. "Carbonyl Chemistry 2: Reactions at the α Position"
(16)
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
20. "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
21. "Special Topic: Bioorganic Chemistry"
(7)
Steroids
Metathesis
Terpenes Reactions
Terpene Synthesis
Synthesis of Fatty Acids
Biosynthesis of Cholesterol
Biosynthesis of Terpenes
22. "Special Topic: Amino Acids and Polyamino Acids (Peptides and Proteins)"
(5)
Amino Acids
Zwitter Ions
Peptide Synthesis
General Properties of Proteins
Strecker Synthesis
23. "Special Topic: Reactions Controlled by Orbital Symmetry"
(1)
Cope Rearrangement
24. "Special Topic: Intramolecular Reactions and Neighboring Group Participation"
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