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Map: Organic Chemistry (Smith)

Organic Chemistry Chemistry

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01: Structure and Bonding
1.01: The Periodic Table
1.02: Bonding
1.03: Lewis Structures
1.04: Lewis Structures Continued
1.05: Bond Length and Bond Strength
1.06: Electronegativity and Bond Polarity
1.07: Polarity of Molecules
1.08: L-DopaA Representative Organic Molecule
1.09: Resonance
1.10: Determining Molecular Shape
1.11: Drawing Organic Structures
1.12: Hybridization
1.13: Ethane Ethylene and Acetylene
02: Acids and Bases
2.01: BrnstedLowry Acids and Bases
2.02: Reactions of BrnstedLowry Acids and Bases
2.03: Acid Strength and (pK a)
2.04: Predicting the Outcome of AcidBase Reactions
2.05: Factors That Determine Acid Strength
2.06: Common Acids and Bases
2.07: Aspirin
2.08: Lewis Acids and Bases
03: Introduction to Organic Molecules and Functional Groups
3.01: Functional Groups
3.02: An Overview of Functional Groups
3.03: Intermolecular Forces
3.04: Physical Properties
3.05: Application - Vitamins
3.06: Application of Solubility- Soap
3.07: Application- The Cell Membrane
3.08: Functional Groups and Reactivity
3.09: Biomolecules
04: Alkanes
4.01: AlkanesAn Introduction
4.02: Cycloalkanes
4.03: An Introduction to Nomenclature
4.04: Naming Alkanes
4.05: Naming Cycloalkanes
4.06: Common Names
4.07: Fossil Fuels
4.08: Physical Properties of Alkanes
4.09: Conformations of Butane
4.10: An Introduction to Cycloalkanes
4.11: Cyclohexane
4.12: Substituted Cycloalkanes
4.13: Oxidation of Alkanes
4.14: LipidsPart 1
4.15: Conformations of Acyclic AlkanesEthane
05: Stereochemistry
5.01: Starch and Cellulose
5.02: The Two Major Classes of Isomers
5.03: Looking Glass ChemistryChiral and Achiral Molecules
5.04: Stereogenic Centers
5.05: Stereogenic Centers in Cyclic Compounds
5.06: Labeling Stereogenic Centers with R or S
5.07: Diastereomers
5.08: Meso Compounds
5.09: R and S Assignments in Compounds with Two or More Stereogenic Centers
5.10: Disubstituted Cycloalkanes
5.11: IsomersA Summary
5.12: Physical Properties of Stereoisomers
5.13: Chemical Properties of Enantiomers
06: Understanding Organic Reactions
6.01: Writing Equations for Organic Reactions
6.02: Kinds of Organic Reactions
6.03: Bond Breaking and Bond Making
6.04: Bond Dissociation Energy
6.05: Thermodynamics
6.06: Enthalpy and Entropy
6.07: Energy Diagrams
6.08: Energy Diagram for a Two-Step Reaction Mechanism
6.09: Kinetics
6.10: Catalysts
6.11: Enzymes
6.12: Kinds of Organic Reactions
6.13: Thermodynamics
6.14: Energy Diagrams
6.15: Energy Diagram for a Two-Step Reaction Mechanism
6.16: Kinetics
07: Alkyl Halides and Nucleophilic Substitution
7.01: Introduction to Alkyl Halides
7.02: Nomenclature
7.03: Physical Properties
7.04: Interesting Alkyl Halides
7.05: The Polar CarbonHalogen Bond
7.06: General Features of Nucleophilic Substitution
7.07: The Leaving Group
7.08: The Nucleophile
7.09: Possible Mechanisms for Nucleophilic Substitution
7.10: Two Mechanisms for Nucleophilic Substitution
7.11: The (S N2) Mechanism
7.12: Application- Useful (S N2) Reactions
7.13: The (S N1) Mechanism
7.14: Carbocation Stability
7.15: The Hammond Postulate
7.16: Application- (S N1) Reactions Nitrosamines and Cancer
7.17: When Is the Mechanism (S N1) or (S N2)
7.18: Vinyl Halides and Aryl Halides
7.19: Organic Synthesis
08: Alkyl Halides and Elimination Reactions
8.01: General Features of Elimination
8.02: AlkenesThe Products of Elimination Reactions
8.03: The Mechanisms of Elimination
8.04: The (E 2) Mechanism
8.05: The Zaitsev Rule
8.06: The (E 1) Mechanism
8.07: (S N1) and (E 1) Reactions
8.08: Stereochemistry of the (E 2) Reaction
8.09: When is the Mechanism (E 1) or (E 2)
8.10: (E 2) Reactions and Alkyne Synthesis
8.11: When Is the Reaction (S N1) (S N2) (E 1) or (E 2)
09: Alcohols Ethers and Epoxides
9.01: Dehydration Using (POCl 3) and Pyridine
9.02: Conversion of Alcohols to Alkyl Halides with HX
9.03: Conversion of Alcohols to Alkyl Halides with (SOCl 2) and (PBr 3)
9.04: TosylateAnother Good Leaving Group
9.05: Reaction of Ethers with Strong Acid
9.06: Reactions of Epoxides
9.07: Application- Epoxides Leukotrienes and Asthma
9.08: Application- Benzoapyrene Epoxides and Cancer
9.09: Introduction
9.10: Structure and Bonding
9.11: Nomenclature
9.12: Physical Properties
9.13: Interesting Alcohols Ethers and Epoxides
9.14: Preparation of Alcohols Ethers and Epoxides
9.15: General FeaturesReactions of Alcohols Ethers and Epoxides
9.16: Dehydration of Alcohols to Alkenes
9.17: Carbocation Rearrangements
10: Alkenes
10.01: Introduction
10.02: Calculating Degrees of Unsaturation
10.03: Nomenclature
10.04: Physical Properties
10.05: Interesting Alkenes
10.06: LipidsPart 2
10.07: Preparation of Alkenes
10.08: Introduction to Addition Reactions
10.09: HydrohalogenationElectrophilic Addition of HX
10.10: Markovnikovs Rule
10.11: Stereochemistry of Electrophilic Addition of HX
10.12: HydrationElectrophilic Addition of Water
10.13: HalogenationAddition of Halogen
10.14: Stereochemistry of Halogenation
10.15: Halohydrin Formation
10.16: HydroborationOxidation
10.17: Keeping Track of Reactions
10.18: Alkenes in Organic Synthesis
11: Alkynes
11.01: Introduction
11.02: Nomenclature
11.03: Physical Properties
11.04: Interesting Alkynes
11.05: Preparation of Alkynes
11.06: Introduction to Alkyne Reactions
11.07: Addition of Hydrogen Halides
11.08: Addition of Halogen
11.09: Addition of Water
11.10: HydroborationOxidation
11.11: Reaction of Acetylide Anions
11.12: Synthesis
12: Oxidation and Reduction
12.01: Introduction
12.02: Reducing Agents
12.03: Reduction of Alkenes
12.04: Application- Hydrogenation of Oils
12.05: Reduction of Alkynes
12.06: The Reduction of Polar CX Bonds
12.07: Oxidizing Agents
12.08: Epoxidation
12.09: Dihydroxylation
12.10: Oxidative Cleavage of Alkenes
12.11: Oxidative Cleavage of Alkynes
12.12: Oxidation of Alcohols
12.13: Green Chemistry
12.14: Application- The Oxidation of Ethanol
12.15: Sharpless Epoxidation
13: Radical Reactions
13.01: Introduction
13.02: General Features of Radical Reactions
13.03: Halogenation of Alkanes
13.04: The Mechanism of Halogenation
13.05: Chlorination of Other Alkanes
13.06: Chlorination versus Bromination
13.07: Halogenation as a Tool in Organic Synthesis
13.08: The Stereochemistry of Halogenation Reactions
13.09: Application- The Ozone Layer and CFCs
13.10: Radical Halogenation at an Allylic Carbon
13.11: Application- Oxidation of Unsaturated Lipids
13.12: Application- Antioxidants
13.13: Radical Addition Reactions to Double Bonds
13.14: Polymers and Polymerization
14: Conjugation Resonance and Dienes
14.01: Conjugation
14.02: Resonance and Allylic Carbocations
14.03: Common Examples of Resonance
14.04: The Resonance Hybrid
14.05: Electron Delocalization Hybridization and Geometry
14.06: Conjugated Dienes
14.07: Interesting Dienes and Polyenes
14.08: The CarbonCarbon Bond Length in 13-Butadiene
14.09: Stability of Conjugated Dienes
14.10: Electrophilic Addition- 12- Versus 14-Addition
14.11: Kinetic Versus Thermodynamic Products
14.12: The DielsAlder Reaction
14.13: Specific Rules Governing the DielsAlder Reaction
14.14: Other Facts About the DielsAlder Reaction
14.15: Conjugated Dienes and Ultraviolet Light
15: Benzene and Aromatic Compounds
15.01: Background
15.02: The Structure of Benzene
15.03: Nomenclature of Benzene Derivatives
15.04: Spectroscopic Properties
15.05: Interesting Aromatic Compounds
15.06: Benzenes Unusual Stability
15.07: The Criteria for Aromaticity - Huckels Rule
15.08: Examples of Aromatic Compounds
15.09: What Is the Basis of Huckels Rule
15.10: The Inscribed Polygon Method for Predicting Aromaticity
15.11: BuckminsterfullereneIs It Aromatic
16: Electrophilic Aromatic Substitution
16.01: Limitations on Electrophilic Substitution Reactions with Substituted Benzenes
16.02: Disubstituted Benzenes
16.03: Synthesis of Benzene Derivatives
16.04: Halogenation of Alkyl Benzenes
16.05: Oxidation and Reduction of Substituted Benzenes
16.06: Multistep Synthesis
16.07: Electrophilic Aromatic Substitution
16.08: The General Mechanism
16.09: Halogenation
16.10: Nitration and Sulfonation
16.11: FriedelCrafts Alkylation and FriedelCrafts Acylation
16.12: Substituted Benzenes
16.13: Electrophilic Aromatic Substitution of Substituted Benzenes
16.14: Why Substituents Activate or Deactivate a Benzene Ring
16.15: Orientation Effects in Substituted Benzenes
17: Carboxylic Acids and the Acidity of the OH Bond
17.01: Inductive Effects in Aliphatic Carboxylic Acids
17.02: Substituted Benzoic Acids
17.03: Extraction
17.04: Sulfonic Acids
17.05: Amino Acids
17.06: Structure and Bonding
17.07: Nomenclature
17.08: Physical Properties
17.09: Spectroscopic Properties
17.10: Interesting Carboxylic Acids
17.11: Aspirin Arachidonic Acid and Prostaglandins
17.12: Preparation of Carboxylic Acids
17.13: Reactions of Carboxylic AcidsGeneral Features
17.14: Carboxylic AcidsStrong Organic BrnstedLowry Acids
18: Introduction to Carbonyl Chemistry Organometallic Reagents Oxidation and Reduction
18.01: Introduction
18.02: General Reactions of Carbonyl Compounds
18.03: A Preview of Oxidation and Reduction
18.04: Reduction of Aldehydes and Ketones
18.05: The Stereochemistry of Carbonyl Reduction
18.06: Enantioselective Carbonyl Reductions
18.07: Reduction of Carboxylic Acids and Their Derivatives
18.08: Oxidation of Aldehydes
18.09: Organometallic Reagents
18.10: Reaction of Organometallic Reagents with Aldehydes and Ketones
18.11: Retrosynthetic Analysis of Grignard Products
18.12: Protecting Groups
18.13: Reaction of Organometallic Reagents with Carboxylic Acid Derivatives
18.14: Reaction of Organometallic Reagents with Other Compounds
18.15: -Unsaturated Carbonyl Compounds
18.16: SummaryThe Reactions of Organometallic Reagents
18.17: Synthesis
19: Aldehydes and KetonesNucleophilic Addition
19.01: The Wittig Reaction
19.02: Addition of 1 Amines
19.03: Addition of 2 Amines
19.04: Addition of (H 2O)Hydration
19.05: Addition of AlcoholsAcetal Formation
19.06: Acetals as Protecting Groups
19.07: Cyclic Hemiacetals
19.08: An Introduction to Carbohydrates
19.09: Introduction
19.10: Nomenclature
19.11: Physical Properties
19.12: Spectroscopic Properties
19.13: Interesting Aldehydes and Ketones
19.14: Preparation of Aldehydes and Ketones
19.15: Reactions of Aldehydes and KetonesGeneral Considerations
19.16: Nucleophilic Addition of H and RA Review
19.17: Nucleophilic Addition of CN
20: Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution
20.01: Reactions of Carboxylic Acids
20.02: Reactions of Esters
20.03: Application- Lipid Hydrolysis
20.04: Reactions of Amides
20.05: Application- The Mechanism of Action of -Lactam Antibiotics
20.06: Summary of Nucleophilic Acyl Substitution Reactions
20.07: Natural and Synthetic Fibers
20.08: Biological Acylation Reactions
20.09: Nitriles
20.10: Introduction
20.11: Structure and Bonding
20.12: Nomenclature
20.13: Physical Properties
20.14: Spectroscopic Properties
20.15: Interesting Esters and Amides
20.16: Introduction to Nucleophilic Acyl Substitution
20.16.01: 22.8 Reactions of Acid Chlorides
20.17: Reactions of Acid Chlorides
20.18: Reactions of Anhydrides
21: Substitution Reactions of Carbonyl Compounds at the Alpha Carbon
21.01: Acetoacetic Ester Synthesis
21.02: Introduction
21.03: Enols
21.04: Enolates
21.05: Enolates of Unsymmetrical Carbonyl Compounds
21.06: Racemization at the Carbon
21.07: A Preview of Reactions at the Carbon
21.08: Halogenation at the Carbon
21.09: Direct Enolate Alkylation
21.10: Malonic Ester Synthesis
22: Carbonyl Condensation Reactions
22.01: The Aldol Reaction
22.02: Crossed Aldol Reactions
22.03: Directed Aldol Reactions
22.04: Intramolecular Aldol Reactions
22.05: The Claisen Reaction
22.06: The Crossed Claisen and Related Reactions
22.07: The Dieckmann Reaction
22.08: The Michael Reaction
22.09: The Robinson Annulation
23: Amines
23.01: Relative Basicity of Amines and Other Compounds
23.02: Amines as Nucleophiles
23.03: Hofmann Elimination
23.04: Reaction of Amines with Nitrous Acid
23.05: Substitution Reactions of Aryl Diazonium Salts
23.06: Coupling Reactions of Aryl Diazonium Salts
23.07: Application- Synthetic Dyes
23.08: Application- Sulfa Drugs
23.09: Introduction
23.9.01: 25.2 Structure and Bonding
23.10: Structure and Bonding
23.11: Nomenclature
23.12: Physical Properties
23.13: Spectroscopic Properties
23.14: Interesting and Useful Amines
23.15: Preparation of Amines
23.16: Reactions of AminesGeneral Features
23.17: Amines as Bases
24: Synthetic Polymers
24.01: Introduction
24.02: Chain-Growth PolymersAddition Polymers
24.03: Anionic Polymerization of Epoxides
24.04: ZieglerNatta Catalysts and Polymer Stereochemistry
24.05: Natural and Synthetic Rubbers
24.06: Step-Growth PolymersCondensation Polymers
24.07: Polymer Structure and Properties
24.08: Green Polymer Synthesis
24.09: Polymer Recycling and Disposal