The Art of Writing Reasonable Organic Reaction Mechanisms
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Beschreibung
Chapter 1. The Basics.
1. Structure and Stability of Organic Compounds
o Conventions of Drawing Structures; Grossman's Rule
o Lewis Structures; Resonance Structures
o Molecular Shape; Hybridizationo Aromaticity
2. Bronsted Acidity and Basicity
o pKa Values
o Tautomerism
3. Kinetics and Thermodynamics
4. Getting Started at Drawing a Mechanismo Reading and balancing organic reaction equations
o Determining which bonds are made and broken in a reaction
5. Classes of Overall Transformations
6. Classes of Mechanisms
o Polar Mechanisms
Nucleophiles
Electrophiles and Leaving Groups
Acidic and Basic Conditions; The pKa Rule
A Typical Polar Mechanism
o Free-Radical Mechanisms
o Pericyclic Mechanisms
o Transition-Metal-Catalyzed and -Mediated Mechanisms
7. Summary
8. End of Chapter Problems
Chapter 2. Polar Reactions under Basic Conditions.
1. Introduction to Substitution and Elimination
o Substitution by the SN2 Mechanism
o beta-Elimination by the E2 and E1cb Mechanismso Predicting Substitution vs. Elimination
2. Addition of Nucleophiles to Electrophilic pi Bonds
o Addition to Carbonyl Compounds
o Conjugate Addition; The Michael Reaction3. Substitution at C(sp2)-X s Bonds
o Substitution at Carbonyl C
o Substitution at Alkenyl and Aryl C
o Metal Insertion; Halogen-Metal Exchange
4. Substitution and Elimination at C(sp3)-X s Bondso Substitution by the SRN1 Mechanism
o Substitution by the Elimination-Addition Mechanism
o Substitution by the One-Electron Transfer Mechanism
o Metal Insertion; Halogen-Metal Exchangeo -Elimination; Generation and Reactions of Carbenes
5. Base-Promoted Rearrangements
o Migrations from C to C
o Migrations from C to Oo Migrations from C to N
o Migrations from B to C or O
6. Two Multistep Reactions
o The Swern Oxidation
o The Mitsunobu Reaction7. Summary
8. End of Chapter Problems
Chapter 3. Polar Reactions under Acidic Conditions.
1. Carbocations
o Carbocation Stabilityo Carbocation Generation; The Role of Protonation
o Typical Reactions of Carbocations; Rearrangements
2. Substitution and beta-Elimination Reactions at C(sp3)-X
o Substitution by the SN1 and SN2 Mechanisms
o Elimination by the E1 Mechanismo Predicting Substitution vs. Elimination
3. Electrophilic Addition to Nucleophilic C=C pi Bonds
4. Substitution at Nucleophilic C=C pi Bonds
o Electrophilic Aromatic Substitutiono Aromatic Substitution of Anilines via Diazonium Salts
o Electrophilic Aliphatic Substitution
5. Nucleophilic Addition to and Substitution at Electrophilic pi Bonds.
o Heteroatom Nucleophileso Carbon Nucleophiles
6. Catalysis Involving Iminium Ions
7. Summary
8. End of Chapter Problems
Chapter 4. Pericyclic Reactions.
1. Introduction
o Classes of Pericyclic Reactions
o Polyene MOs
2. Electrocyclic Reactionso Typical Reactions
o Stereospecificity
o Stereoselectivity
3. Cycloadditionso Typical Reactions
The Diels-Alder Reaction
Other Cycloadditions
o Regioselectivityo Stereospecificity
o Stereoselectivity
4. Sigmatropic Rearrangements
o Typical Reactionso Stereospecificity
o Stereoselectivity
5. Ene Reactions.
6. Summary7. End of Chapter Problems
Chapter 5. Free Radical Reactions.
1. Free Radicals
o Stability
o Generation from Closed-Shell Species
o Typical Reactionso Chain vs. Nonchain Mechanisms
2. Chain Free-Radical Reactions
o Substitution Reactions
o Addition and Fragmentation ReactionsCarbon-Heteroatom Bond-Forming Reactions
Carbon-Carbon Bond-Forming and -Cleaving Reactions
3. Nonchain Free-Radical Reactions
o Photochemical Reactions
o Reductions and Oxidations with Metals
Addition of H2 across pi Bonds
Reduction of C-X Bonds. Reductive Coupling
One-Electron Oxidations
o Cycloaromatizations
4. Miscellaneous Radical Reactions
o 1,2-Anionic Rearrangements; Lone-Pair Inversion
o Triplet Carbenes and Nitrenes
5. Summary6. End of Chapter Problems
Chapter 6. Transition-Metal-Mediated and -Catalyzed Reactions.
1. Introduction to the Chemistry of Transition Metals
o Conventions of Drawing Structures
o Counting Electrons
Typical Ligands; Total Electron CountOxidation State and d Electron Count
o Typical Reactions
o Stoichiometric vs. Catalytic Mechanisms
2. Addition Reactionso Late-Metal-Catalyzed Hydrogenation and Hydrometallation (Pd, Pt, Rh)
o Hydroformylation (Co, Rh)
o Hydrozirconation (Zr)
o Alkene Polymerization (Ti, Zr, Sc, and others)o Cyclopropanation, Epoxidation, and Aziridination of Alkenes (Cu, Rh, Mn, Ti)
o Dihydroxylation and Aminohydroxylation of Alkenes (Os)
o Nucleophilic Addition to Alkenes and Alkynes (Hg, Pd)
o Conjugate Addition Reactions (Cu)o Reductive Coupling Reactions (Ti, Zr)
o Pauson-Khand Reaction (Co)
o Dötz Reaction (Cr)
o Metal-Catalyzed Cycloaddition and Cyclotrimerization (Co, Ni, Rh)3. Substitution Reactions
o Hydrogenolysis (Pd)
o Carbonylation of Alkyl Halides (Pd, Rh)
o Heck Reaction (Pd)
o Metal-Caatalyzed Nucleophilic Substitution Reactions: Kumada, Stille, Suzuki, Negishi, Buchwald-Hartwig, Sonogashira, and Ullmann Reactions (Ni, Pd, Cu)
o Allylic Substitution (Pd)
o Pd-Catalyzed Nucleophilic Substitution of Alkenes; Wacker Oxidation
o C-H Activation (Pd, Ru, Rh)
o Tebbe Reaction (Ti)
o Propargyl Substitution in Co-Alkyne Complexes4. Rearrangement Reactions
o Alkene Isomerization (Rh)
o Olefin and Alkyne Metathesis (Ru, W, Mo, Ti)
5. Elimination Reactionso Oxidation of Alcohols (Cr, Ru)
o Decarbonylation of Aldehydes (Rh)
6. Summary
7. End of Chapter Problems
Chapter 7. Mixed Mechanism Problems.
Eigenschaften
| Breite: | 163 |
| Gewicht: | 837 g |
| Höhe: | 239 |
| Länge: | 243 |
| Seiten: | 435 |
| Sprachen: | Englisch |
| Autor: | Robert B. Grossman |
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