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Organic Chemistry, 9th Ed. Wade
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Organic Chemistry, 9th Ed. Wade
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Leroy G Wade Jr, Jan William Simek
Organic Chemistry, 9th Ed. Wade
ISBN: ISBN-13: 978-0321971371, ISBN-10: 032197137X
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1: "Structure 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: "Acids and Bases; Functional Groups"
(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
3: "Structure and Stereochermistry of Alkanes"
(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
4: "The Study of Chemical Reactions"
(15)
Functional Groups
General Forces
Boiling Point
Melting Point
Solubility
Intro to Synthesis and Retrosynthesis
General Reactions
Conversion to alkanes
Bond Dissociation Energy
Free radical halogenation
Free Radcial Reactions
Reactivity-Selectivity Principle
Determining the Stereochemsitry of Radical Halogenation
Allylic bromination [NBS]
Miscellaneous Radical Reactions
5: "Stereochemistry"
(11)
Nomenclature of Stereoisomers
Identifying Stereocenters
Diastereomers
Meso Compounds
Optical Activity
Properties of Stereoisomers
Seperation Techniques
Fischer Projections
Enantiomers
Stereoisomers
Haworth Formula
6: "Alkyl Halides; Nucleophilic Substitution"
(17)
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
Rearangement Considerations for Sn1
Hydride Shift
Methy Shift
Ring Expansion
Ring Reduction
7: "Structure and Synthesis of Alkenes; Elimination"
(18)
Synthesis of Alkenes
Sharpless Epoxidation
Electrophillic Addition
Nucelophilic 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
Rearangement Considerations for E1
Conversion to alcohols
Hoffman Elimination
Zaitsev Elimination
8: "Reactions of Alkenes"
(18)
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
9: "Alkynes"
(13)
Properties of Alkynes
acetylide formation
Nomenclature of Alkynes
Synthesis of Alkynes
Reduction Reactions with Alkynes (Hydrogenation)
Hydration of Alkynes
Hydroboration of Alkynes
Oxymercuration of Alkynes
Addition of HX of Alkynes
Halogenation of Alkynes
Oxidative cleavage of Alkynes
Conversion to Alkenes
Retrosynthesis - Related to Alkenes and Alkynes
10: "Structure and Synthesis of Alcohols"
(5)
Retrosynthesis - Related to Alcohols
Properties of Alcohols
Nomenclature of Alcohols
Synthesis of Alcohols
Acid & Base properties of alcohols
11: "Reactions of Alcohols"
(11)
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
12: "Infrared Spectroscopy and Mass Spectrometry"
(3)
The Electromagnetic Spectrum
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: "Ethers, Epoxides, and Thioethers"
(12)
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
15: "Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy"
(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
16: "Aromatic Compounds"
(3)
Nomenclature of Aromatic Compounds
Aromaticity
Heterocyclic Compounds
17: "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
18: "Ketones and Aldehydes"
(31)
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
19: "Amines"
(20)
Properties of Amines
Nomenclature of Amines
Synthesis - Azide Reduction
Synthesis - Gabriel Synthesis
Synthesis - Reductive Amination
Amines as Bases
Alkyation of Amines
Acylation of Amines
Hofmann Elimination
Cope Elimination
Hinsberg Test
Formation of Diazonium Salts
Diazonium Salts
Azo Coupling
Stork Enamine Reaction
Mannich Reaction
Enanmine Hydrolysis
Conversion to Amines
Curtius Rearrangement
Hoffman Rearrangement
20: "Carboxylic Acids"
(32)
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 characterisitics of benzoyl compounds
General reactions of Carboxylic acids
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
21: "Carboxylic Acid Derivatives"
(30)
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
22: "Condensation and Alpha Substitutions of Carbonyl Compounds"
(24)
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
Aldol addition reaction
Retro-aldol reaction
Claisen condensation
Dieckmann Condensation
Conjugate Addition
Conjugate addition
Robinson annulation
Michael Addition
23: "Carbohydrates (and Nucleic Acids)"
(15)
General Introduction
Classification of Carbohydrates
Formation of Cyclic Hemiacetal
Mutarotation
Reduction of Monosaccharides
Oxidation of Monosaccharides
Enediol Rearangement 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
23: "(Carbohydrates and) Nucleic Acids"
24: "Amino Acids, Peptides and Protein"
(5)
Amino Acids
Zwitter ions
Peptide Synthesis
General Properties of Protiens
Strecker Synthesis
24: "Lipids"
(7)
Steroids
Metathesis
Terpenes Reactions
Terpene synthesis
Synthesis of Fatty Acids
Biosynthesis of Cholesterol
Biosynthesis of Terpenes
25: "Synthetic Polymers"
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