Organic Chemistry
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- Supplemental Modules (Organic Chemistry)
- Acid Halides
- Nomenclature of Acid Halides
- Properties of Acyl Halides
- Reactions of Acid Halides
- Acid chlorides can be converted to aldehydes using LiAlH(Ot-Bu)3
- Acid chlorides react with alcohols to form esters
- Acid chlorides react with ammonia, 1° amines and 2° amines to form amides
- Acid Chlorides react with carboxylic acids to form anhydrides
- Acid chlorides react with water to form carboxylic acids.
- Addition & Elimination Reactions in Acyl Chlorides
- General reaction mechanism of acid chlorides
- Organocuprate reagents convert acid chlorides to ketones
- Reactions of Acyl Chlorides Involving Nitrogen Compounds
- Reactions of Acyl Chlorides Involving Oxygen Compounds
- Reactions of Acyl Chlorides with Alcohols
- Reactions of Acyl Chlorides with Ammonia
- Reactions of Acyl Chlorides with Primary Amines
- Reactions of Acyl Chlorides with Water
- Using Acyl Chlorides in Friedel-Crafts Reactions
- Synthesis of Acid Halides
- Alkanes
- Alkenes
- Nomenclature of Alkenes
- Properties of Alkenes
- Synthesis of Alkenes
- Alkanes from Reduction of Carboxylates - Kolbe's Electrolytic method
- Alkenes by Dehydration of Alcohols
- Alkenes from Aldehydes and Ketones - Wittig Reaction
- Alkenes from Dehydration of Alcohols
- Alkenes from Dehydrohalogenation of Haloalkanes
- Alkenes from Hydrogenation of Alkynes
- Prepartion of Alkenes
- Zaitsev's Rule
- Reactivity of Alkenes
- Addition of Sulfuric acid to Alkenes
- Addition Reactions of Alkenes
- Addition Reactions of Dienes
- Catalytic Hydrogenation of Alkenes
- Catalytic Hydrogenation of Alkenes II
- Catalytic Hydrogenation of Alkenes II
- Diazomethane, Carbenes, and Cyclopropane Synthesis
- Diels-Alder Cycloaddition
- Electrophilic Addition of Halogens to Alkenes
- Electrophilic Addition of Hydrogen Halides
- Electrophilic Addition of Hydrogen Halides II
- Free Radical Reactions of Alkenes
- Hydration of Alkenes
- Hydroboration-Oxidation of Alkenes
- Oxacyclopropane Synthesis
- Oxidation of Alkenes with Potassium Manganate
- Ozonolysis
- Ozonolysis of Alkenes and Alkynes
- Polymerization of Alkenes
- Reactions of Alkenes with Halogens
- Stereoselectivity in Addition Reactions to Double Bonds
- Vicinal Syn Dihydroxylation
- Alkynes
- Nomenclature of Alkynes
- Properties of Alkynes
- Reactivity of Alkynes
- Addition by Electrophilic Reagents
- Anti-Markovnikov Additions to Triple Bonds
- Catalytic Hydrogenation
- Electrophilic Addition Reactions of Alkynes
- Hydration of Alkynes and Tautomerism
- Hydroboration Reactions and Oxidations
- Nucleophilic Addition Reactions & Reduction
- Nucleophilic Reactivity of Deprotonated Alkynes
- Ozonolysis of Alkenes and Alkynes
- Reducing Alkynes-The Reactivity of the Two π Bonds
- Synthesis of Alkynes
- Alcohols
- Nomenclature of Alcohols
- Properties of Alcohols
- Reactivity of Alcohols
- Dehydrating Alcohols to Make Alkenes
- Electrophilic Substitution at Oxygen
- Elimination Reactions of Alcohols
- Hydroxyl Group Substitution
- Reactions of alcohols with hydrohalic acids (HX)
- Reduction of Alcohols
- Replacing the OH Group by Halogen Atoms
- The Oxidation of Alcohols
- The Reaction Between Alcohols and Sodium
- The Triiodomethane (Iodoform) Reaction
- Thionyl Chloride
- Synthesis of Alcohols
- Aldehydes and Ketones
- Nomenclature of Aldehydes & Ketones
- Properties of Aldehydes & Ketones
- Reactivity of Aldehydes & Ketones
- Addition-Elimination Reactions
- Addition of Alcohols to form Hemiacetals and Acetals
- Addition of Secondary Amines to Form Enamines
- Addition of Water to form Hydrates (Gem-Diols)
- Alpha-carbon Reactions
- Carbonyl Group-Mechanisms of Addition
- Carbonyl Group Reactions
- Clemmensen Reduction
- Conjugate Addition Reactions
- Cyanohydrins
- Irreversible Addition Reactions of Aldehydes and Ketones
- Oxidation of Aldehydes and Ketones
- Reactions with Grignard Reagents
- Reaction with Primary Amines to form Imines
- Reduction of Aldehydes and Ketones
- Reduction of Carbonyls to Alcohols Using Metal Hydrides
- Reductive Amination
- Reversible Addition Reactions of Aldehydes and Ketones
- Simple Addition Reactions
- The Triiodomethane (Iodoform) Reaction
- The Wittig Reaction
- Tollens’ Test
- Wolff-Kishner Reduction
- Synthesis of Aldehydes & Ketones
- Alkyl Halides
- Properties of Alkyl Halides
- Haloalkanes
- Introduction to Alkyl Halides
- Physical Properties of Alkyl Halides
- Reactivity of Alkyl Halides
- Alkyl Halide Reactions
- Reaction of Alkyl Halides with Ammonia
- Reaction of Alkyl Halides with Silver Nitrate
- The Reaction of Alkyl Halides with Cyanide Ions
- The Reaction of Alkyl Halides with Hydroxide Ions
- Synthesis of Alkyl Halides
- Uses of Alkyl Halides
- Properties of Alkyl Halides
- Amides
- Amines
- Anhydrides
- Arenes
- Nomenclature of Arenes
- Properties of Arenes
- Reactivity of Arenes
- Benzene
- Characteristics of Specific Substitution Reactions of Benzenes
- Electrophilic Aromatic Substitution
- Electrophilic Substitution of Disubstituted Benzene Rings
- Nucleophilic Reactions of Benzene Derivatives
- Reactions of Fused Benzene Rings
- Reactions of Substituent Groups
- Substitution Reactions of Benzene Derivatives
- Electrophilic Substitution of Disubstituted Benzene Rings
- Friedel-Crafts Acylation
- Halogenation of Benzene-The Need for a Catalyst
- Halogenation of Benzene and Methylbenzene
- Modifying the Influence of Strong Activating Groups
- Nitration and Sulfonation of Benzene
- Nitration of Benzene and Methylbenzene
- Other Reactions of Benzene and Methylbenzene
- Reactions of Fused Benzene Rings
- Reactions of Substituent Groups
- Substitution Reactions of Benzene and Other Aromatic Compounds
- Substitution Reactions of Benzene Derivatives
- Benzene
- Synthesis of Arenes
- Aryl Halides
- Azides
- Carbohydrates
- Carboxylic Acids
- Nomenclature of Carboxylic Acids
- Properties of Carboxylic Acids
- Reactivity of Carboxylic Acids
- Conversion of a Carboxylic Acid to an Amide
- Conversion of carboxylic acids to acid chlorides
- Conversion of carboxylic acids to alcohols using LiAlH4
- Conversion of Carboxylic acids to amides using DCC as an activating agent
- Fischer Esterification
- Hell-Volhard-Zelinskii Reaction
- Making Acyl Chlorides (Acid Chlorides)
- Making Esters From Carboxylic Acids
- Reactions of Carboxylic Acids
- Reduction of Carboxylic Acids with \(LiAlH_4\)
- Simple Reactions of Carboxylic Acids as Acids
- The Decarboxylation of Carboxylic Acids and Their Salts
- Synthesis of Carboxylic Acids
- Chirality
- Absolute Configuration: R-S Sequence Rules
- Chirality and Stereoisomers
- Diastereomers
- Fischer Projections
- Fundamentals of Chirality
- Meso Compounds
- Mixtures of Stereoisomers
- Optical Activity
- Stereoisomers
- Alkene Stereoisomers
- Butane Conformers
- Chirality and Symmetry
- Compounds with Several Stereogenic Centers
- Configurational Nomenclature
- Conformational Stereoisomers
- Cycloalkane Stereoisomer
- Ethane Conformers
- Resolution
- Stereogenic Nitrogen
- Stereoisomerism in Disubstituted Cyclohexanes
- Stereoisomers: Ring Conformations
- Substituted Cyclohexanes
- Conjugation
- Esters
- Nomenclature of Esters
- Properties of Esters
- Reactivity of Esters
- Acid Catalyzed Hydrolysis of Esters
- Acid Catalyzed Hydrolysis of Esters (II)
- Esters can be converted aldehydes using diisobutylaluminum hydride (DIBAH).
- Esters can be reduced to 1° alcohols using \(LiAlH_4\)
- General mechanism of ester reactions
- Grignard Reagents Convert Esters into Tertiary Alcohols
- Polyesters
- Saponification
- The Hydrolysis of Esters
- Transesterification
- Synthesis of Esters
- Ethers
- Fundamentals
- Bonding in Organic Compounds
- Bonding in Benzene: the Kekulé Structure
- Bonding in Benzene - a Modern Orbital View
- Bonding in Carbonyl Compounds
- Bonding in Ethene
- Bonding in Ethyne (Acetylene)
- Bonding in Methane
- Calculating of π-bonds, σ-bonds, single and double bonds in Straight Chain and Cycloalkene Systems
- Identifing Aromatic and Anti-Aromatic Compounds
- Predicting the Hybridization of Heterocyclic Compounds
- Chemical Reactivity
- Electronegativity
- Molecular Classes
- Functional groups A
- Homolytic C-H Bond Dissociation Energies of Organic Molecules
- How to Draw Organic Molecules
- Hybrid Orbitals
- Index of Hydrogen Deficiency (IHD)
- Intermolecular Forces
- Structure & Bonding
- Ionic and Covalent Bonds
- Isomerism in Organic Compounds
- Lewis Structures
- Nomenclature
- Organic Acids and Bases
- Oxidation States of Organic Molecules
- Practice Problems
- Reactive Intermediates
- Resonance Forms
- Rotation in Substituted Ethanes
- Structure of Organic Molecules
- The Golden Rules of Organic Chemistry
- The Use of Curly Arrows
- What is the pKa of water?
- Bonding in Organic Compounds
- Hydrocarbons
- Lipids
- Nitriles
- Organo-phosphorus Compounds
- Phenols
- Phenylamine and Diazonium Compounds
- Polymers
- Addition Polymers
- Condensation Polymers
- Copolymers
- EXPLAINING THE "PEROXIDE EFFECT" IN THE REACTION BETWEEN HYDROGEN BROMIDE AND ALKENES
- Hydrogen Bromide and Aklenes: The Peroxide Effect
- Introduction to Polymers
- Molecular Weights of Polymers
- Polyethylene
- Polymer Fundamentals
- Properties of Polymers
- Recycling and Disposal of Polymers
- Regio and Stereoisomerization in Polymers
- Rubber Polymers
- Silicone Polymers
- Synthesis of Addition Polymers
- Thermosetting vs. Thermoplastic Polymers
- The Polymerization of Ethene
- Writing Formulas for Polymers
- Reactions
- Reaction Fundamentals
- Addition Reactions
- Addition to Carbonyls
- Carbonyls are Electrophiles
- CO10. Activation of Carbonyls
- CO11. Addition of Neutral, Protic Nucleophiles
- CO12. Proton Transfer Steps
- CO13. \(\pi\) Donation Steps
- CO15. The Anomeric Center
- CO16. Biological Reduction
- CO17. Oxidation
- CO19. Conjugate Addition
- CO2. General Reactivity Patterns
- CO20. Conjugate Addition-Elimination in Aromatics
- CO21. Carbonyl Addition Summary: Mechanistic Steps
- CO23. Solutions to Selected Problems, CO1-9
- CO24. Solutions to Selected Problems, CO10-18
- CO3. MO Picture of Carbonyls
- CO4. Relative Reactivity of Carbonyls
- CO5. Nucleophilic Addition
- CO6. Protonation of Oxygen
- CO7. What is a Good Nucleophile?
- CO8. Semi-Anionic Nucleophiles
- CO9. Enolate Addition and Homologation
- Pyranose and Furanose Forms
- Ylide Addition
- Electrophilic Addition Reactions
- Nucleophilic Addition Reactions
- Addition to Carbonyls
- Reactivity
- Electrophilic Addition to Alkenes
- Electrophilic Aromatic Substitution
- Ligand Substitution in Coordination Complexes
- Nucleophilic Substitution at Tetrahedral Carbon
- NS1. Introduction to ANS
- NS10. Leaving Group Formation
- NS11. NA to Strained Rings
- NS12. Elimination Reactions
- NS13. Regiochem. in Elimination
- NS14. Stereochem in Elimination
- NS15. Elim. Mechanism Factors
- NS16. Solutions for Problems
- NS2. Possible Mechanisms of NS
- Rate Laws in Nucleophilic Substitution
- NS4. Stereochemistry in NS
- NS5. Regiochemistry in NS
- NS6. Structural Effects in NS
- NS7. Solvent Effects in NS
- NS8. Nucleophilicity in NS
- NS9. Enolate Nucleophiles
- Oxidative Addition & Reductive Elimination
- Part V: Reactivity in Organic, Biological and Inorganic Chemistry 3
- Roadmap Problems in Natural Product synthesis
- RR. Radical Reactions
- Reactivity of Alpha Hydrogens
- Elimination Reactions
- Substitution Reactions
- Carboxyl Substitution
- Comparative Energies: The Ski Hill
- CX11. Protein Modifications
- CX12. Solutions For Selected Problems
- CX2. General Reactivity Patterns
- CX5. Getting Towed Uphill
- CX6. Semi-Anionic Nucleophiles
- CX7. Enolates: Substitution and Decarboxylation
- CX8. Condensation Polymers
- CX9. Peptides and Proteins: Laboratory Synthesis
- Interconversion of Carboxyloids: Going Downhill
- Introduction to Carboxyloids (Acid Derivatives)
- Electrophilic Substitution Reactions
- IV. Nucleophilic Substitution Reactions
- Kinetics of Nucleophilic Substitution Reactions
- SN1
- SN2
- Carboxyl Substitution
- Rearrangement Reactions
- Free Radical Reactions
- Oxidation and Reduction Reactions
- Named Reactions
- Appel Reaction
- Baeyer-Villiger oxidation
- Bartoli indole synthesis
- Baylis-Hillman reaction
- Beckmann Rearrangement
- Biginelli reaction
- Birch Reduction
- Buchwald-Hartwig amination
- Cannizzaro reaction
- Chugaev Reaction
- Claisen rearrangement
- Cope Elimination
- Corey-Kim oxidation
- Curtius Rearrangement
- Dakin-West reaction
- Dakin Oxidation
- Dieckmann condensation
- Diels-Alder reaction
- Eschenmoser-Claisen rearrangement
- Eschweiler-Clarke reaction
- Finkelstein reaction
- Fischer esterification
- Fischer indole synthesis
- Friedel-Crafts acylation
- Friedel-Crafts alkylation
- Fries rearrangement
- Gabriel synthesis
- Grignard reaction
- Heck reaction
- Hell-Volhard-Zelinsky reaction
- Henry reaction
- Hofmann Elimination
- Hofmann rearrangement
- Horner-Wadsworth-Emmons Reaction
- Ireland-Claisen rearrangement
- Johnson-Claisen rearrangement
- Jones oxidation
- Knoevenagel condensation
- Knorr pyrazole synthesis
- Kolbe-Schmitt reaction
- Kumada cross-coupling
- Luche reduction
- Mannich reaction
- Michael addition
- Mitsunobu Macrolactonization
- Mitsunobu reaction
- Mukaiyama aldol addition
- Named Reagents
- Negishi cross-coupling
- Oppenauer oxidation
- Overman Rearrangement
- Pauson-Khand reaction
- Perkin reaction
- Pictet-Spengler reaction
- Prins reaction
- Pummerer Rearrangement
- Reformatsky reaction
- Reimer-Tiemann reaction
- Ritter reaction
- Robinson annulation
- Schmidt reaction
- Schotten-Baumann reaction
- Sharpless epoxidation
- Sonogashira cross-coupling
- Staudinger reaction
- Stille cross-coupling
- Strecker amino acid synthesis
- Suzuki cross-coupling
- Swern oxidation
- Tamao-Fleming Oxidation
- TES protection
- Ullmann reaction
- Vilsmeier-Haack reaction
- Wagner-Meerwein rearrangement
- Williamson ether synthesis
- Wittig reaction
- Wolff-Kishner reduction
- Wolff rearrangement
- Yamaguchi Esterification
- Organic Reactions
- Aldol Condensation
- Cannizzaro Reaction
- Claisen Condensation
- Claisen Rearrangement
- Clemmensen Reduction
- Dieckmann Condensation
- Formation of Cyclic Ketones by Intramolecular Acylation
- Hydroamination Reactions of Alkenes
- Jacobsen Rearrangement
- Mannich Reaction
- Periodic Acid Oxidation
- Preparation of Aliphatic Fluorine Compounds
- Preparation of Unsymmetrical Biaryls by the Diazo Reaction and the Nitrosoacetylamine Reaction
- Reduction with Aluminum Alkoxides (The Meerwein-Ponndorf-Verley Reduction)
- Replacement of the Aromatic Primary Amino Group by Hydrogen
- Schmidt Reaction
- Wacker Oxidation
- Wittig Reaction
- Pericyclic Reactions
- Zimmerman-Traxler Model
- Keck Asymmetric Allylation
- Chan Rearrangement
- Introduction to Bioconjugation
- Thiols and Sulfides
- Spectroscopy
- Acid Halides
- Book: Organic Chemistry Lab Techniques (Nichols)
- 1: General Techniques
- 2: Chromatography
- 3: Crystallization
- 4: Extraction
- 5: Distillation
- 6: Miscellaneous Techniques
- 7: Technique Summaries
- 7.1: Flame-Drying Glassware
- 7.2: Using Calibrated Glass Pipettes
- 7.3: Inert Atmospheric Methods
- 7.4: Reflux
- 7.5: Suction Filtration
- 7.6: Hot Filtration
- 7.7: Thin Layer Chromatography
- 7.8: TLC Visualization Methods
- 7.9: Macroscale Column Chromatography
- 7.10: Pipette Column Chromatography
- 7.11: Testing Solvents for Crystallization
- 7.12: Testing Mixed Solvents for Crystallization
- 7.13 Single Solvent Crystallization
- 7.14: Mixed Solvent Crystallization
- 7.15: Single Extraction
- 7.16 Multiple Extraction
- 7.17: Microscale Extractions
- 7.18: Testing the pH After a Wash
- 7.19: Using Drying Agents
- 7.20: Acid-Base Extraction
- 7.21: Simple Distillation
- 7.22: Fractional Distillation
- 7.23: Vacuum Distillation
- 7.24: Steam Distillation
- 7.25: Rotary Evaporation
- 7.26: Melting Points
- 7.27: Boiling Points (Thiele Tube)
- 7.28: Vacuum Sublimation
- About the Author - Lisa Nichols
- Book: Organic Chemistry with a Biological Emphasis (Soderberg)
- Introduction
- 1: Introduction to organic structure and bonding I
- 2: Introduction to Organic Structure and Bonding II
- 3: Conformations and Stereochemistry
- 3.1: Conformations of open-chain organic molecules
- 3.2: Conformations of cyclic organic molecules
- 3.3: Chirality and stereoisomers
- 3.4: Naming chiral centers: the R and S system
- 3.5: Optical Activity
- 3.6: Compounds with multiple chiral centers
- 3.7: Meso compounds
- 3.8: Fischer and Haworth projections
- 3.10: Stereochemistry in biology and medicine
- 3.11: Prochirality
- 3.9: Stereochemistry of alkenes
- 3.P: Problems for Chapter 3
- Solutions to Chapter 3 exercises
- 4: Structure Determination I: UV-Vis and Infrared Spectroscopy, Mass Spectrometry
- 5: Structure Determination II - Nuclear Magnetic Resonance Spectroscopy
- 5.1: The origin of the NMR signal
- 5.2: Chemical equivalence
- 5.3: The NMR experiment
- 5.4: The basis for differences in chemical shift
- 5.5: Spin-spin coupling
- 5.6: 13C-NMR spectroscopy
- 5.7 : Determining unknown structures
- 5.8: NMR of phosphorylated molecules
- 5.P: Problems for Chapter 5
- 5.S: Nuclear Magnetic Resonance Spectroscopy (Summary)
- 6: Introduction to Organic Reactivity and Catalysis
- 7: Acids and bases
- 7.1: Overview of acid-base reactions
- 7.2: The acidity constant
- 7.3: Structural effects on acidity and basicity
- 7.4: Acid-base properties of phenols
- 7.5: Acid-base properties of nitrogen-containing functional groups
- 7.6: Carbon acids
- 7.7: Polyprotic acids
- 7.8: The effects of solvent and enzyme microenvironment on acidity
- 7.P: Problems for Chapter 7
- 8: Nucleophilic substitution reactions, part I
- 8.1: Introduction to the nucleophilic substitution reaction
- 8.2: Two mechanistic models for a nucleophilic substitution reaction
- 8.3: More about nucleophiles
- 8.4: Electrophiles and carbocation stability
- 8.5: Leaving groups
- 8.6: Epoxides as electrophiles in nucleophilic substitution reactions
- 8.P: Problems for Chapter 8
- 9: Nucleophilic substitution reactions, part II
- 9.1: Methyl group transfers: examples of SN2 reactions
- 9.2: Digestion of carbohydrate by glycosidase - an SN1 reaction
- 9.3: Protein prenyltransferase - a hybrid SN1/SN2 substitution
- 9.4: Biochemical nucleophilic substitutions with epoxide electrophiles
- 9.5: Nucleophilic substitution over conjugated pi systems - the SN' mechanism
- 9.P: Problems for Chapter 9
- 10: Phosphoryl transfer reactions
- 11: Nucleophilic carbonyl addition reactions
- 11.1: Nucleophilic additions to aldehydes and ketones: the general picture
- 11.2: Stereochemistry of the nucleophilic addition reaction
- 11.3: Hemiacetals, hemiketals, and hydrates
- 11.4: Acetals and ketals
- 11.5: N-glycosidic bonds
- 11.6: Imine (Schiff base) formation
- 11.7: A look ahead: addition of carbon and hydride nucleophiles to carbonyls
- 11.P: Problems for Chapter 11
- 12: Acyl substitution reactions
- 12.1: Introduction to carboxylic acid derivatives and the nucleophilic acyl substitution reaction
- 12.2: Acyl phosphates as activated carboxylic acids
- 12.3: Thioesters
- 12.4: Esters
- 12.5: Nucleophilic acyl substitution reactions involving peptide bonds
- 12.6: Activated amide groups
- 12.7: A look ahead: acyl substitution reactions with a carbon or hydride nucleophile
- 12.P: Problems for Chapter 12
- 13: Reactions with stabilized carbanion intermediates I
- 14: Reactions with stabilized carbanion intermediates, part II
- 14.1: Michael additions, β eliminations and reactions with electron sink cofactors
- 14.2: Variations on the Michael reaction
- 14.3: Elimination by the E1 and E2 mechanisms
- 14.4: Pyridoxal phosphate - an electron sink cofactor
- 14.5: Thiamine diphosphate-dependent reactions
- 14.6: The transition state geometry of reactions involving pi bonds
- 14.P: Problems for Chapter 14
- 15: Electrophilic reactions
- 15.1: An overview of the different types of electrophilic reactions
- 15.2: Electrophilic addition
- 15.3: Electrophilic isomeration and substitution
- 15.4: Another kind of electrophilic addition-elimination - shikimate to chorismate
- 15.5: Electrophilic aromatic substitution reactions
- 15.6: Synthetic parallel - electrophilic aromatic substitution in the lab
- 15.7: Carbocation rearrangements
- 15.8: Cation-pi interactions and the stabilization of carbocation intermediates
- 15.9: Outside the box - 1,3-elimination and rearrangement in squalene synthase
- 15.10: The Diels-Alder reaction and other pericyclic reactions
- 15.P: Problems for Chapter 15
- 16: Oxidation and reduction reactions
- 16.1: Oxidation and reduction of organic compounds - an overview
- 16.2: The importance of redox reactions in metabolism
- 16.3: Outside the box - methanogenesis
- 16.4: Hydrogenation/dehydrogenation reactions of carbonyls, imines, and alcohols
- 16.5: Hydrogenation of alkenes and dehydrogenation of alkanes
- 16.6: Additional examples of enzymatic hydride transfer reactions
- 16.7: NAD(P)H, FADH2 and metabolism - a second look
- 16.8: Observing the progress of hydrogenation and dehydrogenation reactions by UV spectroscopy
- 16.9: Hydrogenation/dehydrogenation reactions and renewable energy technology
- 16.10: Oxygenase reactions- flavin-dependent monoxygenases
- 16.11: Halogenation of organic compounds
- 16.12: Redox reactions involving thiols and disulfides
- 16.13: Redox reactions in the organic synthesis laboratory
- 16.P: Problems for Chapter 16
- 17: Radical reactions
- Full Table of Contents
- Reference Tables
- Examples of common functional groups in organic chemistry
- Representative acid constants
- Some characteristic absorption frequencies in IR spectroscopy
- Some common laboratory solvents, acids, and bases
- Structures of common coenzymes
- The 20 common amino acids
- Typical coupling constants in NMR
- Typical values for carbon NMR chemical shifts
- Typical values for proton NMR chemical shifts
- Retrosynthetic analysis and metabolic pathway prediction
- Solution Manual
- Chapter 1 Solutions
- Chapter 2 Solutions
- Solutions to selected chapter 3 problems
- Chapter 4 Solutions
- Chapter 5 Solutions
- Chapter 6 Solutions
- Chapter 7 Solutions
- Chapter 8 Solutions
- Chapter 9 Solutions
- Chapter 10 Solutions
- Chapter 11 Solutions
- Chapter 12 Solutions
- Chapter 13 Solutions
- Chapter 14 Solutions
- Chapter 15 Solutions
- Chapter 16 Solutions
- Chapter 17 Solutions
- Appendix I: Index of enzymatic reactions by pathway
- Appendix: Review of laboratory synthesis reactions
- Book: Basic Principles of Organic Chemistry (Roberts and Caserio)
- 1: Introduction to Organic Chemistry
- 2: Structural Organic Chemistry
- 3: Organic Nomenclature
- 4: Alkanes
- 4.0: Prelude to Alkanes
- 4.1: Physical Properties of Alkanes and The Concept of Homology
- 4.2: Chemical Reactions of Alkanes. Combustion of Alkanes
- 4.3: Combustion. Heats of Reaction. Bond Energies
- 4.4: Halogenation of Alkanes. Energies and Rates of Reactions
- 4.5: Practical Halogenations and Problems of Selectivity
- 4.6: Nitration of Alkanes
- 4.E: Alkanes (Exercises)
- 5. Stereoisomerism of Organic Molecules
- 5.0: Prelude to Stereoisomerism
- 5.1: Configurational Isomers
- 5.2: Conformational Isomers
- 5.3: Representation of Organic Structure
- 5.4: The D, L Convention for Designating Stereochemical Configurations
- 5.5: Molecules with More Than One Chiral Center. Diastereomers
- 5.6: Some Examples of the Importance of Stereoisomerism to Biology. Biological Stereospeciflcity
- 5.E: Stereoisomerism of Organic Molecules (Exercises)
- 6: Bonding in Organic Molecules
- 7: Other Compounds than Hydrocarbons
- 7.1: General Approaches to Naming Organic Compounds
- 7.2: Alcohols and Phenols: ROH, ArOH
- 7.3: Ethers, ROR'
- 7.4: Aldehydes
- 7.5: Ketones, RCOR'
- 7.6: Carboxylic Acids
- 7.7: Acyl Groups, RCO-
- 7.8: Amines
- 7.9: Nitriles, RCN
- 7.10: The Use of Greek Letters to Denote Substituent Positions
- 7.11: Single- or Multiple-Word Names
- 7.E: Other Compounds than Hydrocarbons (Exercises)
- 8: Nucleophilic Substitution and Elimination Reactions
- 8.0: Prelude to Nucleophilic Substitution and Elimination Reactions
- 8.1: Classification of Reagents as Electrophiles and Nucleophiles. Acids and Bases
- 8.2: Thermochemistry of Substitution Reactions
- 8.3: General Considerations of Substitution Reactions
- 8.4: Mechanisms of Nucleophilic Substitution Reactions
- 8.5: Stereochemistry of \(S_N2\) Reactions
- 8.6: Stereochemistry of \(S_N1\) Reactions
- 8.7: Structural and Solvent Effects in \(S_N\) Reactions
- 8.8: The E2 Reaction
- 8.9: The E1 Reaction
- 8.E: Nucleophilic Substitution and Elimination Reactions (Exercises)
- Elimination Reactions
- 9: Separation, Purification, & Identification of Organic Compounds
- 9.0: Prelude to Separation, Purification, & Identification
- 9.1: How do we know when an Organic Compounds is Pure?
- 9.2: Chromatographic Separation Procedures
- 9.3: Why Can't We See Molecules?
- 9.4: Atomic Energy States and Line Spectra
- 9.5: Energy States of Molecules
- 9.6: Microwave (Rotational) Spectra
- 9.7: Infrared (Rovibrational) Spectroscopy
- 9.8: Raman Spectroscopy
- 9.9: Electronic Spectra of Organic Molecules
- 9.10: Nuclear Magnetic Resonance Spectroscopy
- 9.11: Mass Spectroscopy
- 9.E: Separation, Purification, & Identification of Organic Compounds (Exercises)
- 10: Alkenes and Alkynes I - Ionic and Radical Addition Reactions
- 10.0: Prelude to Alkenes and Alkynes
- 10.1: Physical and Spectroscopic Properties of Alkenes and Alkynes
- 10.2: The Reactivity of Multiple Carbon-Carbon Bonds
- 10.3: Electrophilic Additions to Alkenes
- 10.4: Orientation in Addition to Alkenes
- 10.5: Electrophilic Addition Reactions of Alkynes
- 10.6: Nucleophilic Addition Reactions
- 10.7: Radical-Chain Addition Reactions to Alkenes
- 10.8: Polymerization of Alkenes
- 10.9: Alkylation of Alkenes
- 10.E: Alkenes and Alkynes I (Exercises)
- 11: Alkenes and Alkynes II - Oxidation and Reduction Reactions. Acidity of Alkynes
- 11.1: Oxidation-Reduction of Organic Compounds
- 11.2: Hydrogenation with Heterogeneous Catalysts
- 11.3: Heats of Hydrogenation
- 11.4: Hydrogenation with Homogeneous Catalysts
- 11.5: Hydrogenation with Diimide
- 11.6: Addition of Boron Hydrides to Alkenes. Organoboranes
- 11.7: Oxidation Reactions
- 11.8: Terminal Alkynes as Acids
- 11.E: Alkenes and Alkynes II (Exercises)
- 12: Cycloalkanes, Cycloalkenes and Cycloalkynes
- 12.1: Nomenclature and Physical Properties of Cycloalkanes
- 12.2: Spectroscopic Properties of Cyclohexanes
- 12.3: Conformations of Cycloalkanes
- 12.4: Strain in Cycloalkane Rings
- 12.5: Chemical Properties
- 12.6: The Larger Cycloalkanes and their Conformations
- 12.7: Cycloalkenes and Cycloalkanes
- 12.8: Nomenclature of Polycycloalkanes
- 12.9: Conformations of Decalin
- 12.10: Strain in Polycyclic Molecules
- 12.E: Cycloalkanes, Cycloalkenes, and Cycloalkynes (Exercises)
- 13: Polyfunctional Compounds, Alkadienes, and Approaches to Organic Synthesis
- 13.1: General Comments on Alkadienes
- 13.2: 1,3- or Conjugated Dienes. Electrophilic and Radical Addition
- 13.3: Cycloaddition Reactions
- 13.4: Polymerization Reactions of Conjugated Dienes
- 13.5: Cumulated Alkadienes
- 13.6: Approaches to Planning Practical Organic Syntheses
- 13.7: Building the Carbon Skeleton
- 13.8: Introducing Functionality
- 13.9: Construction of Ring Systems by Cycloaddition
- 13.10: Protecting Groups in Organic Synthesis
- 13.E: Polyfunctional Compounds, Alkadienes, and Approaches to Organic Synthesis (Exercises)
- 14: Organohalogen & Organometallic Compounds
- 14.0: Prelude to Organohalogen & Organometallic Compounds
- 14.1: Physical Properties of Organohalogen & Organometallic Compounds
- 14.2: Spectroscopic Properties
- 14.3: Alkyl Halides
- 14.4: Alkenyl and Alkynyl Halides
- 14.5: Cycloalkyl Halides
- 14.6: Aryl Halides
- 14.7: Polyhalogenated Alkanes and Alkenes
- 14.8: Organometallic Compounds from Organohalogen Compounds
- 14.9: Properties of Organometallic Compounds
- 14.10: Preparation of Organometallic Compounds
- 14.11: Organomagnesium Compounds
- 14.12: Organomagnesium & Organolithium Compounds in Synthesis
- 14.E: Organohalogen & Organometallic Compounds (Exercises)
- 15: Alcohols and Ethers
- 15.0: Prelude to Alcohols and Ethers
- 15.1: Physical Properties of Alcohols; Hydrogen Bonding
- 15.2: Spectroscopic Properties of Alcohols
- 15.3: Preparation of Alcohols
- 15.4: Chemical Reactions of Alcohols. Reactions Involving the O-H Bond
- 15.5: Reactions Involving the C-O Bond of Alcohols
- 15.6: Oxidation of Alcohols
- 15.7: Polyhydric Alcohols
- 15.8: Unsaturated Alcohols - Alkenols
- 15.9: Protection of Hydroxyl Groups
- 15.10: Types and Reactions of Simple Ethers
- 15.11: Cyclic Ethers
- 15.E: Alcohols and Ethers (Exercises)
- 16: Carbonyl Compounds I: Aldehydes and Ketones. Addition Reactions of the Carbonyl Group
- 16.0: Prelude to Aldehydes and Ketones
- 16.1: The Carbonyl Bond
- 16.2: Physical Properties
- 16.3: Spectroscopic Properties
- 16.4: Typical Carbonyl-Addition Reactions
- 16.5: Catalytic Hydrogenation
- 16.6: Reduction of Carbonyl Compounds to Hydrocarbons
- 16.7: Oxidation of Carbonyl Compounds
- 16.8: Protection of Carbonyl Groups
- 16.9: Preparative Methods for Aldehydes and Ketones
- 16.E: Carbonyl Compounds I (Exercises)
- Tables: General Methods for the Preparation of Aldehydes and Ketones
- 17: Carbonyl Compounds II: Enols and Enolate Anions. Unsaturated and Polycarbonyl Compounds
- 17.0: Prelude to Enols and Enolate Anions, Unsaturated, & Polycarbonyl Compounds
- 17.1: Enolization of Aldehydes and Ketones
- 17.2: Halogenation of Aldehydes and Ketones
- 17.3: Nucleophilic Addition Reactions of Enolate Anions
- 17.4: Nucleophilic Substitution with Enolate Anions
- 17.5: α,β-Unsaturated Aldehydes and Ketones
- 17.6: Ketenes
- 17.7: 1,2-Dicarbonyl Compounds
- 17.8: 1,3-Dicarbonyl Compounds
- 17.9: 1,4-Dicarbonyl Compounds
- 17.10: Tricarbonyl Compounds
- 17.11: Cyclopropanones and Cyclopropenones
- 17.E: Carbonyl Compounds II (Exercises)
- 18: Carboxylic Acids and Their Derivatives
- 18.0: Prelude to Carboxylic Acids and Their Derivatives
- 18.1: Physical Properties of Carboxylic Acids
- 18.2: Some Chemical Properties of Carboxylic Acids
- 18.3: Reactions at the Carbonyl Carbon of Carboxylic Acids
- 18.4: Decarboxylation of Carboxylic Acids
- 18.5: Reactions at the \(\alpha\) Carbons of Carboxylic Acids
- 18.6: Functional Derivatives of Carboxylic Acids
- 18.7: Reactions at the Carbonyl Carbon of Acid Derivatives
- 18.8: Reactions at the \(\alpha\) Carbons of Carboxylic Acid Derivatives
- 18.9: Reactions of Unsaturated Carboxylic Acids and Their Derivatives
- 18.10: Dicarboxylic Acids
- 18.E: Carboxylic Acids and Their Derivatives (Exercises)
- Tables: Methods of Preparation of Carboxylic Acids and Their Derivatives
- 19: More on Stereochemistry
- 19.1: Plane-Polarized Light and the Origin of Optical Rotation
- 19.2: Specific Rotation
- 19.3: Separation or Resolution of Enantiomers
- 19.4: Enantiomeric Purity
- 19.5: Absolute And Relative Configuration
- 19.6: The R,S Convention for Designating Stereochemical Configurations
- 19.7: E,Z Notation
- 19.8: Prochirality
- 19.9: Optical Rotatory Dispersion and Circular Dichroism
- 19.10: Asymmetric Synthesis
- 19.11: Racemization
- 19.E: More on Stereochemistry (Exercises)
- 20: Carbohydrates
- 20.0: Prelude to Carbohydrates
- 20.1: Classification and Occurrence of Carbohydrates
- 20.2: The Structure and Properties of D-Glucose
- 20.3: Conventions for Indicating Ring Size and Anomer Configurations of Monosaccharides
- 20.4: Derivatives of Glucose
- 20.5: Glycosides
- 20.6: Disaccharides
- 20.7: Polysaccharides
- 20.8: Vitamin C
- 20.9: Formation of Carbohydrates by Photosynthesis
- 20.10: The Generation of Energy from Carbohydrate Metabolism
- 20.E: Carbohydrates (Exercises)
- 21: Resonance and Molecular Orbital Methods
- 21.0: Prelude to Resonance and Molecular Orbital Methods
- 21.1: Characteristics of Simple Covalent Bonds
- 21.2: Comparison of the Resonance and Molecular-Orbital Methods
- 21.3: The Benzene Problem
- 21.4: Application of the MO Method to 1,3-Butadiene
- 21.5: Application of MO Theory to Other Systems
- 21.6: Which Is Better: MO or VB?
- 21.7: More on Stabilization Energies
- 21.8: Bond Lengths and Double-Bond Character
- 21.9: Hückel's 4n + 2 Rule
- 21.10: Pericyclic Reactions
- 21.11: Evidence Bearing on the Mechanism of [2 + 2] Cycloadditions
- 21.E: Resonance and Molecular Orbital Methods (Exercises)
- 22: Arenes, Electrophilic Aromatic Substitution
- 22.1: Nomenclature of Arenes
- 22.2: Physical Properties of Arenes
- 22.3: Spectral Properties of Arenes
- 22.4: Electrophilic Aromatic Substitution
- 22.5: Effect of Substituents on Reactivity and Orientation in Electrophilic Aromatic Substitution
- 22.6: Orientation in Disubstituted Benzenes
- 22.7: IPSO Substitution
- 22.8: Substitution Reactions of Polynuclear Aromatic Hydrocarbons
- 22.9: Addition Reactions of Arenes
- 22.10: Oxidation Reactions
- 22.11: Sources and Uses of Aromatic Hydrocarbons
- 22.12: Some Conjugated Cyclic Polyenes
- 22.13: Fluxional Compounds
- 22.E: Arenes, Electrophilic Aromatic Substitution (Exercises)
- 23: Organonitrogen Compounds I: Amines
- 23.1: Amines Compared with Alcohols
- 23.2: Naturally Occurring Amines
- 23.3: Types and Nomenclature of Amines
- 23.4: Physical Properties of Amines
- 23.5: Spectroscopic Properties of Amines
- 23.6: Stereochemistry of Amines
- 23.7: Amines as Bases
- 23.8: Amines as Acids
- 23.9: Amines as Nucleophiles
- 23.10: Amines with Nitrous Acid
- 23.11: Oxidation of Amines
- 23.12: Synthesis of Amines
- 23.13: Protection of Amino Groups in Synthesis
- 23.14: Carcinogenic Nitrogen Compounds
- 23.E: Organonitrogen Compounds I: Amines (Exercises)
- 24: Organonitrogen Compounds II: Amides, Nitriles, & Nitro Compounds
- 24.1: Structural, Physical, and Spectral Characteristics of Amides
- 24.2: Amides as Acids and Bases
- 24.3: Synthesis of Amides
- 24.4: Hydrolysis of Amides
- 24.5: Nitriles
- 24.6: Nitro Compounds
- 24.7: Some Compounds with N-N Bonds
- 24.E: Organonitrogen Compounds II: Amides, Nitriles, & Nitro Compounds (Exercises)
- 25: Amino Acids, Peptides, and Proteins
- 25.1: Types of Biologically Important Amino Acids
- 25.2: Acid-Base Properties of \(\alpha\)-Amino Acids
- 25.3: Physical and Spectroscopic Properties
- 25.4: Analysis of Amino Acids
- 25.5: Reactions of Amino Acids
- 25.6: Synthesis of α-Amino Acids
- 25.7: Peptides and Proteins
- 25.8: Structure and Function of Proteins
- 25.9: Enzymes
- 25.10: Coenzymes
- 25.11: Enzyme Regulation
- 25.12: Enzyme Technology
- 25.13: Biosynthesis of Proteins
- 25.14: Chemical Evolution
- 25.E: Amino Acids, Peptides, and Proteins (Exercises)
- 26: More on Aromatic Compounds
- 26.1: Aryl Oxygen Compounds
- 26.2: Quinones
- 26.3: Tropolones & Related Compounds
- 26.4: Some Aromatic Side-Chain Compounds
- 26.5: Natural Occurrence and Uses of Some Aromatic Side-Chain Compounds
- 26.6: Correlations of Structure with Reactivity of Aromatic Compounds
- 26.E: More on Aromatic Compounds (Exercises)
- 27: More about Spectroscopy
- 27.0: Prelude to More Spectroscopy
- 27.1: Line-Width Differences in NMR
- 27.2: Use of the Uncertainty Principle to Measure the Rates of Chemical Transformations
- 27.3: Why Spin-Spin Splitting?
- 27.4: Chemically Induced Dynamic Nuclear Polarization (CIDNP)
- 27.5: Photoelectron Spectroscopy
- 27.6: Mössbauer Spectroscopy
- 27.7: Field- and Chemical-Ionization Mass Spectroscopy
- 27.8: Ion-Cyclotron Resonance
- 27.9: Electron-Spin Resonance (ESR) Spectroscopy of Organic Radicals
- 27.E: More about Spectroscopy (Exercises)
- 28: Photochemistry
- 29: Polymers
- 29.0: Prelude
- 29.1: A Simple Addition Polymerization. The Parts of a Polymer
- 29.2: Types of Polymers
- 29.3: Forces Between Polymer Chains
- 29.4: Correlation of Polymer Properties with Structure
- 29.5: Condensation Polymers
- 29.6: Addition Polymers
- 29.7: Block, Graft, and Ladder Polymers
- 29.8: Naturally Occurring Polymers
- 29.E: Polymers (Exercises)
- Preparation of Synthetic Polymers
- 30: Natural Products and Biosynthesis
- 31: Transition Metal Organic Compounds
- 31.1: Metallocenes
- 31.2: Other Organometallic Compounds of Transition Metals
- 31.3: Transition-Metal Compounds as Reagents for Organic Syntheses
- 31.4: Some Homogeneous Catalytic Reactions Involving Transition-Metal Complexes
- 31.5: π-Propenyl Complexes of Nickel
- 31.6: Vitamin B₁₂ as an Organometallic Compound
- 31.E: Transition Metal Organic Compounds (Exercises)
- Map: Organic Chemistry (McMurry)
- Chapter 1: Structure and Bonding
- 1.0: Prelude to Structure and Bonding
- 1.1: Atomic Structure - The Nucleus
- 1.2: Atomic Structure - Orbitals
- 1.3: Atomic Structure - Electron Configurations
- 1.4: Development of Chemical Bonding Theory
- 1.5: The Nature of Chemical Bonds - Valence Bond Theory
- 1.6: sp³ Hybrid Orbitals and the Structure of Methane
- 1.7: sp³ Hybrid Orbitals and the Structure of Ethane
- 1.8: sp² Hybrid Orbitals and the Structure of Ethylene
- 1.9: sp Hybrid Orbitals and the Structure of Acetylene
- 1.10: Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur
- 1.11: The Nature of Chemical Bonds: Molecular Orbital Theory
- 1.12: Drawing Chemical Structures
- 1.S: Structure and Bonding (Summary)
- Chapter 2: Polar Covalent Bonds; Acids and Bases
- 2.1: Polar Covalent Bonds: Electronegativity
- 2.2: Polar Covalent Bonds - Dipole Moments
- 2.3: Formal Charges
- 2.4: Resonance
- 2.5: Rules for Resonance Forms
- 2.6: Drawing Resonance Forms
- 2.7: Acids and Bases - The Brønsted-Lowry Definition
- 2.8: Acid and Base Strength
- 2.9: Predicting Acid-Base Reactions from pKa Values
- 2.10: Organic Acids and Organic Bases
- 2.11: Acids and Bases - The Lewis Definition
- 2.13: Molecular Models
- 2.S: Polar Covalent Bonds; Acids and Bases (Summary)
- Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
- Chapter 4: Organic Compounds: Cycloalkanes and their Stereochemistry
- Chapter Objectives
- 4.1: Naming Cycloalkanes
- 4.2: Cis-Trans Isomerism in Cycloalkanes
- 4.3: Stability of Cycloalkanes - Ring Strain
- 4.4: Conformations of Cycloalkanes
- 4.5: Conformations of Cyclohexane
- 4.6: Axial and Equatiorial Bonds in Cyclohexane
- 4.7: Conformations of Monosubstituted Cyclohexanes
- 4.8: Conformations of Disubstituted Cyclohexanes
- 4.9: Conformations of Polycyclic Molecules
- Chapter 5: Stereochemistry at Tetrahedral Centres
- Chapter Objectives
- 5.1: Enantiomers and the Tetrahedral Carbon
- 5.2: The Reason for Handedness in Molecules - Chirality
- 5.3: Optical Activity
- 5.4: Pasteur's Discovery of Enantiomers
- 5.5: Sequence Rules for Specifying Configuration
- 5.6: Diastereomers
- 5.7: Meso Compounds
- 5.8: Racemic Mixtures and the Resolution of Enantiomers
- 5.9: A Review of Isomerism
- 5.10: Chirality at Nitrogen, Phosphorus, and Sulfur
- 5.11: Prochirality
- 5.12: Chirality in Nature and Chiral Environments
- 5:3 Enantiomers & Diastereomers
- Meso Compounds
- Chapter 6: An Overview of Organic Reactions
- Chapter Objectives
- 6.1: Kinds of Organic Reactions
- 6.2: How Organic Reactions Occur - Mechanisms
- 6.3: Radical Reactions
- 6.4: Polar Reactions
- 6.5: An Example of a Polar Reaction - Addition of HBr to Ethylene
- 6.6: Using Curved Arrows in Polar Reaction Mechanisms
- 6.7: Describing a Reaction - Equilibria, Rates, and Energy Changes
- 6.8: Describing a Reaction - Bond Dissociation Energies
- 6.9: Describing a Reaction - Energy Diagrams and Transition States
- 6.10: Describing a Reaction: Intermediates
- 6.11: A Comparison between Biological Reactions and Laboratory Reactions
- Chapter 7: Alkenes - Structure and Reactivity
- Chapter Objectives
- 7.0: Introduction to Alkenes
- 7.1: Industrial Preparation and Use of Alkenes
- 7.2: Calculating Degree of Unsaturation
- 7.3: Naming Alkenes
- 7.4: Cis-Trans Isomerism in Alkenes
- 7.5: Sequence Rules - The E,Z Designation
- 7.6: Stability of Alkenes
- 7.7: Electrophilic Addition Reactions of Alkenes
- 7.8: Orientation of Electrophilic Additions - Markovnikov's Rule
- 7.9: Carbocation Structure and Stability
- 7.10: The Hammond Postulate
- 7.11: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements
- Chapter 8: Alkenes: Reactions and Synthesis
- Chapter Objectives
- 8.1: Preparation of Alkenes - A Preview of Elimination Reactions
- 8.2: Halogenation of Alkenes - Addition of X₂
- 8.3: Halohydrins from Alkenes - Addition of HOX
- 8.4: Hydration of Alkenes - Addition of H₂O by Oxymercuration
- 8.5: Hydration of Alkenes: Addition of H₂O by Hydroboration
- 8.6: Reduction of Alkenes - Hydrogenation
- 8.7: Oxidation of Alkenes - Epoxidation and Hydroxylation
- 8.8: Oxidation of Alkenes - Cleavage to Carbonyl Compounds
- 8.9: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
- 8.10: Radical Additions to Alkenes - Chain-Growth Polymers
- 8.11: Biological Additions of Radicals to Alkenes
- 8.12: Stereochemistry of Reactions - Addition of H₂O to an Achiral Alkene
- 8.13: Stereochemistry of Reactions - Addition of H₂O to a Chiral Alkene
- Chapter 9: Alkynes - An Introduction to Organic Synthesis
- Chapter Objectives
- 9.1: Naming Alkynes
- 9.2: Preparation of Alkynes - Elimination Reactions of Dihalides
- 9.3: Reactions of Alkynes - Addition of HX and X₂
- 9.4: Hydration of Alkynes
- 9.5: Reduction of Alkynes
- 9.6: Oxidative Cleavage of Alkynes
- 9.7: Alkyne Acidity - Formation of Acetylide Anions
- 9.8: Alkylation of Acetylide Anions
- 9.9: An Introduction to Organic Synthesis
- Chapter 10: Organohalides
- Chapter Objectives
- 10.0: Introduction to Organohalides
- 10.1: Names and Properties of Alkyl Halides
- 10.2: Preparing Alkyl Halides from Alkanes - Radical Halogenation
- 10.3: Preparing Alkyl Halides from Alkenes - Allylic Bromination
- 10.4: Stability of the Allyl Radical - Resonance Revisited
- 10.5: Preparing Alkyl Halides from Alcohols
- 10.6: Reactions of Alkyl Halides - Grignard Reagents
- 10.7: Organometallic Coupling Reactions
- 10.8: Oxidation and Reduction in Organic Chemistry
- Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
- Chapter Objectives
- 11.0: Introduction
- 11.1: The Discovery of Nucleophilic Substitution Reactions
- 11.2: The Sₙ2 Reaction
- 11.3: Characteristics of the Sₙ2 Reaction
- 11.4: The Sₙ1 Reaction
- 11.5: Characteristics of the Sₙ1 Reaction
- 11.6: Biological Substitution Reactions
- 11.7: Elimination Reactions: Zaitsev's Rule
- 11.8: The E2 Reaction and the Deuterium Isotope Effect
- 11.9: The E2 Reaction and Cyclohexane Conformation
- 11.10: The E1 and E1cB Reactions
- 11.11: Biological Elimination Reactions
- 11.12: A Summary of Reactivity - \(S_{N}1\), \(S_{N}2\), E1, E1cB, and E2
- Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
- Chapter Objectives
- 12.0: Introduction
- 12.1: Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments
- 12.2: Interpreting Mass Spectra
- 12.3: Mass Spectrometry of Some Common Functional Groups
- 12.4: Mass Spectrometry in Biological: Time-of-flight (TOF) Instruments
- 12.5: Spectroscopy and the Electromagnetic Spectrum
- 12.6: Infrared Spectroscopy
- 12.7: Interpreting Infrared Spectra
- 12.8: Infrared Spectra of Some Common Functional Groups
- Chapter 13: Structure Determination - Nuclear Magnetic Resonance Spectroscopy
- Chapter Objectives
- 13.1: Nuclear Magnetic Resonance Spectroscopy
- 13.2: The Nature of NMR Absorptions
- 13.3: Chemical Shifts
- 13.4: ¹³C NMR Spectroscopy - Signal Averaging and FT-NMR
- 13.5: Characteristics of ¹³C NMR Spectroscopy
- 13.6: DEPT ¹³C NMR Spectroscopy
- 13.7: Uses of ¹³C NMR Spectroscopy
- 13.8: ¹H NMR Spectroscopy and Proton Equivalence
- 13.9: Chemical Shifts in ¹H NMR Spectroscopy
- 13.10: Integration of ¹H NMR Absorptions: Proton Counting
- 13.10: Integration of ¹H NMR Absorptions: Proton Counting
- 13.11: Spin-Spin Splitting in ¹H NMR Spectra
- 13.12: More Complex Spin-Spin Splitting Patterns
- 13.13: Uses of ¹H NMR Spectroscopy
- Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy
- Chapter Objectives
- 14.0: Introduction
- 14.1: Stability of Conjugated Dienes - Molecular Orbital Theory
- 14.2: Electrophilic Additions to Conjugated Dienes - Allylic Carbocations
- 14.3: Kinetic vs. Thermodynamic Control of Reactions
- 14.4: The Diels-Alder Cycloaddition Reaction
- 14.5: Characteristics of the Diels-Alder Reaction
- 14.6: Diene Polymers - Natural and Synthetic Rubbers
- 14.7: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy
- 14.8: Interpreting Ultraviolet Spectra - The Effect of Conjugation
- 14.9: Conjugation, Color, and the Chemistry of Vision
- Chapter 15: Benzene and Aromaticity
- Chapter Objectives
- 15.0: Introduction
- 15.1: Sources and Names of Aromatic Compounds
- 15.2: Structure and Stability of Benzene
- 15.3: Aromaticity and the Hückel 4n + 2 Rule
- 15.4: Aromatic Ions
- 15.5: Aromatic Heterocycles - Pyridine and Pyrrole
- 15.6: Polycyclic Aromatic Compounds
- 15.7: Spectroscopy of Aromatic Compounds
- Chapter 16: Chemistry of Benzene - Electrophilic Aromatic Substitution
- Chapter Objectives
- 16.0: Introduction
- 16.1: Electrophilic Aromatic Substitution Reactions - Bromination
- 16.2: Other Aromatic Substitutions
- 16.3: Alkylation and Acylation of Aromatic Rings - The Friedel-Crafts Reaction
- 16.4: Substituent Effects in Substituted Aromatic Rings
- 16.5: An Explanation of Substituent Effects
- 16.6: Trisubstituted Benzenes - Additivity of Effects
- 16.7: Nucleophilic Aromatic Substitution
- 16.8: Benzyne
- 16.9: Oxidation of Aromatic Compounds
- 16.10: Reduction of Aromatic Compounds
- 16.11: Synthesis of Polysubstituted Benzenes
- Chapter 17: Alcohols and Phenols
- Chapter Objectives
- 17.0 Introduction
- 17.1 Naming Alcohols and Phenols
- 17.2 Properties of Alcohols and Phenols
- 17.3 Preparation of Alcohols: A Review
- 17.4 Alcohols from Carbonyl Compounds: Reduction
- 17.5 Alcohols from Reaction of Carbonyl Compounds: Grignard Reagents
- 17.6 Reactions of Alcohols
- 17.7 Oxidation of Alcohols
- 17.8 Protection of Alcohols
- 17.9 Phenols and Their Uses
- 17.10 Reactions of Phenols
- 17.11 Spectroscopy of Alcohols and Phenols
- Chapter 18: Ethers and Epoxides; Thiols and Sulfides
- Chapter Objectives
- 18.0: Introduction
- 18.1: Names and Properties of Ethers
- 18.2: Synthesis of Ethers
- 18.3: Reactions of Ethers - Acidic Cleavage
- 18.4: Reactions of Ethers - Claisen Rearrangement
- 18.5: Cyclic Ethers - Epoxides
- 18.6: Reactions of Epoxides - Ring-opening
- 18.7: Crown Ethers
- 18.8: Thiols and Sulfides
- 18.9: Spectroscopy of Ethers
- 18.10: Affix - A Preview of Carbonyl Compounds
- Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions
- Chapter Objectives
- 19.1 Naming Aldehydes and Ketones
- 19.2 Preparing Aldehydes and Ketones
- 19.3 Oxidation of Aldehydes and Ketones
- 19.4 Nucleophilic Addition Reactions of Aldehydes and Ketones
- 19.5 Nucleophilic Addition of \(H_2O\): Hydration
- 19.6 Nucleophilic Addition of HCN: Cyanohydrin Formation
- 19.7 Nucleophilic Addition of Grignard Reagents and Hydride Reagents: Alcohol Formation
- 19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation
- 19.9 Nucleophilic Addition of Hydrazin - The Wolff-Kishner Reaction
- 19.10 Nucleophilic Addition of Alcohols: Acetal Formation
- 19.11 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
- 19.12 Biological Reductions
- 19.13 Conjugate Nucleophilic Addition to \(\alpha\), \(\beta\)-unsaturated Aldehydes and Ketones
- 19.14 Spectroscopy of Aldehydes and Ketones
- Chapter 20: Carboxylic Acids and Nitriles
- Chapter Objectives
- 20.0 Introduction
- 20.1 Naming Carboxylic Acids and Nitriles
- 20.2 Structure and Properties of Carboxylic Acids
- 20.3 Biological Acids and the Henderson-Hasselbalch Equation
- 20.4 Substituent Effects on Acidity
- 20.5 Preparing Carboxylic Acids
- 20.6 Reactions of Carboxylic Acids: An Overview
- 20.7 Chemistry of Nitriles
- 20.8 Spectroscopy of Carboxylic Acids and Nitriles
- Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
- Chapter Objectives
- 21.0 Introduction
- 21.1 Naming Carboxylic Acid Derivatives
- 21.2 Nucleophilic Acyl Substitution Reactions
- 21.3 Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
- 21.4 Chemistry of Acid Halides
- 21.5 Chemistry of Acid Anhydrides
- 21.6 Chemistry of Esters
- 21.7 Chemistry of Amides
- 21.8 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
- 21.9 Polyamides and Polyesters: Step-Growth Polymers
- 21.10 Spectroscopy of Carboxylic Acid Derivatives
- Chapter 22: Carbonyl Alpha-Substitution Reactions
- Chapter Objectives
- 22.0 Introduction
- 22.1 Keto-Enol Tautomerism
- 22.2 Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions
- 22.3 Alpha Halogenation of Aldehydes and Ketones
- 22.4 Alpha Bromination of Carboxylic Acids
- 22.5 Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
- 22.6 Reactivity of Enolate Ions
- 22.7 Alkylation of Enolate Ions
- Chapter 23: Carbonyl Condensation Reactions
- Chapter Objectives
- 23.1 Carbonyl Condensations - The Aldol Reaction
- 23.2 Carbonyl Condensations versus Alpha Substitutions
- 23.3 Dehydration of Aldol Products - Synthesis of Enones
- 23.4 Using Aldol Reactions in Synthesis
- 23.5 Mixed Aldol Reactions
- 23.6 Intramolecular Aldol Reactions
- 23.7 The Claisen Condensation Reaction
- 23.8: Mixed Claisen Condensations
- 23.9 Intramolecular Claisen Condensations - The Dieckmann Cyclization
- 23.10 Conjugate Carbonyl Additions - The Michael Reaction
- 23.11 Carbonyl Condensations with Enamines - The Stork Reaction
- 23.12 The Robinson Annulation Reaction
- 23.13 Some Biological Carbonyl Condensation Reactions
- Chapter 24: Amines and Heterocycles
- Chapter Objectives
- 24.1 Naming Amines
- 24.2 Structure and Properties of Amines
- 24.3 Basicity of Amines
- 24.4 Basicity of Arylamines
- 24.5 Biological Amines and the Henderson-Hasselbalch Equation
- 24.6 Synthesis of Amines
- 24.7 Reactions of Amines
- 24.8 Reactions of Arylamines
- 24.9 Heterocyclic Amines
- 24.10 Spectroscopy of Amines
- Chapter 25: Biomolecules: Carbohydrates
- Chapter Objectives
- 25.0 Introduction
- 25.1 Classification of Carbohydrates
- 25.2 Depicting Carbohydrate Stereochemistry: Fischer Projections
- 25.3 D, L Sugars
- 25.4 Configurations of Aldoses
- 25.5 Cyclic Structures of Monosaccharides: Anomers
- 25.6: Reactions of Monosaccharides
- 25.7 The Eight Essential Monosaccharides
- 25.8 Disaccharides
- 25.9 Polysaccharides and Their Synthesis
- 25.10 Other Important Carbohydrates
- 25.11 Cell-Surface Carbohydrates and Influenza Viruses
- Chapter 26: Biomolecules: Amino Acids, Peptides, and Proteins
- Chapter Objectives
- 26.0 Introduction
- 26.1 Structures of Amino Acids
- 26.2 Amino Acids, the Henderson-Hasselbalch Equation, and Isoelectric Points
- 26.3 Synthesis of Amino Acids
- 26.4 Peptides and Proteins
- 26.5 Amino Acid Analysis of Peptides
- 26.6 Peptide Sequencing: The Edman Degradation
- 26.7 Peptide Synthesis
- 26.8 Automated Peptide Synthesis: The Merrifield Solid-Phase Technique
- 26.9 Protein Structure
- 26.10 Enzymes and Coenzymes
- 26.11 How do Enzymes Work? Citrate Synthase
- Chapter 27: Biomolecules - Lipids
- Chapter 28: Biomolecules - Nucleic Acids
- Chapter 1: Structure and Bonding
- Map: Organic Chemistry (Vollhardt and Schore)
- 1: Structure and Bonding in Organic Molecules
- 1.1: The Scope of Organic Chemistry
- 1.2: Coulomb Forces - A Simplified View of Bonding
- 1.3: Ionic and Covalent Bonds - The Octet Rule
- 1.4: Electron-Dot Model of Bonding - Lewis Structures
- 1.5: Resonance Forms
- 1.6: Atomic Orbitals: A Quantum Mechanical Description of Electrons Around the Nucleus
- 1.7: Molecular Orbitals and Covalent Bonding
- 1.8: Hybrid Orbitals: Bonding in Complex Molecules and Practice Problems
- 1.9: Structures and Formulas of Organic Molecules
- 1.E: Structure and Bonding in Organic Molecules (Exercises)
- 2: Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules
- 2.1: Kinetics and Thermodynamics of Simple Chemical Processes
- 2.2: Keys to Success: Using Curved "Electron Pushing" Arrows to Describe Chemical Reactions
- 2.3: Acids and Bases; Electrophiles and Nucleophiles
- 2.4: Functional Groups: Centers of Reactivity
- 2.5: Straight-Chain and Branched Alkanes
- 2.6: Naming the Alkanes
- 2.7: Structural and Physical Properties of Alkanes
- 2.8: Rotation about Single Bonds: Conformations
- 2.9: Rotation in Substituted Ethanes
- 2.E: Structure and Reactivity: Acids and Bases, Polar and Nonpolar Molecules (Exercises)
- 3: Reactions of Alkanes: Bond-Dissociation Energies, Radical Halogenation, and Relative Reactivity
- 3.1: Strength of Alkane Bonds: Radicals
- 3.2: Structure of Alkyl Radicals: Hyperconjugation
- 3.3: Conversion of Petroleum: Pyrolysis
- 3.4: Chlorination of Methane: The Radical Chain Mechanism
- 3.5: Other Radical Halogenations of Methane
- 3.6: Keys to Success: Using the "Known" Mechanism as a model for the "Unknown"
- 3.7: Chlorination of Higher Alkanes: Relative Reactivity and Selectivity
- 3.8: Selectivity in Radical Halogenation with Fluorine and Bromine
- 3.9: Synthetic Radical Halogenation
- 3.10: Synthetic Chlorine Compounds and the Stratospheric Ozone Layer
- 3.11: Combustion and the Relative Stabilities of Alkanes
- 3.E: Reactions of Alkanes (Exercises)
- 4: Cycloalkanes
- 5: Stereoisomers
- 5.1: Chiral Molecules
- 5.2: Optical Activity
- 5.3: Absolute Configuration: R-S Sequence Rules
- 5.4: Fischer Projections
- 5.5: Molecules Incorporating Several Stereocenters: Diastereomers
- 5.6: Meso Compounds
- 5.7: Stereochemistry in Chemical Reactions
- 5.8: Resolution: Separation of Enantiomers
- 5.E: Stereoisomers (Exercises)
- 6: Bimolecular Nucleophilic Substitution in Haloalkanes
- 6.1: Physical Properties of Haloalkanes
- 6.2: Nucleophilic Substitution
- 6.3: Reaction Mechanisms Involving Polar Functional Groups: Using "Electron-Pushing'" Arrows
- 6.4: A Closer Look at the Nucleophilic Substitution Mechanism: Kinetics
- 6.5: Frontside or Backside Attack? Stereochemistry of the SN2 Reaction
- 6.6: Consequences of Inversion in SN2 Reactions
- 6.7: Structure and \(S_N2\) Reactivity: The Leaving Group
- 6.8: Structure and SN2 Reactivity: The Nucleophile
- 6.9: Keys to Success: Choosing Among Multiple Mechanistic Pathways
- 6.3: Reaction Mechanisms Involving Polar Functional Groups: Using "Electron-Pushing\\'" Arrows
- 6.10: Structure and SN2 Reactivity: The Substrate
- 6.11: The Sn2 Reaction at a Glance
- 6.E: Properties and Reactions of Haloalkanes: Bimolecular Nucleophilic Substitution (Exercises)
- 7: Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination
- 7.1: Solvolysis of Tertiary and Secondary Haloalkanes
- 7.2: Unimolecular Nucleophilic Substitution
- 7.3: Stereochemical Consequences of SN1 Reactions
- 7.4: Effects of Solvent, Leaving Group, and Nucleophile on Unimolecular Substitution
- 7.5: Effect of the Alkyl Group on the SN 1 Reaction: Carbocation Stability
- 7.6: Unimolecular Elimination: E1
- 7.7: Bimolecular Elimination: E2
- 7.8: Keys to Success: Substitutin Versus Elimination-Structure Determines Function
- 7.9: Summary of Reactivity of Haloalkanes
- 7.E: Further Reactions of Haloalkanes: Unimolecular Substitution (Exercises)
- 8: Hydroxy of Functional Group: Alcohols: Properties, Preparation, and Strategy of Synthesis
- 8.1: Naming the Alcohols
- 8.2: Structural and Physical Properties of Alcohols
- 8.3: Alcohols as Acids and Bases
- 8.4: Industrial Sources of Alcohols: Carbon Monoxide and Ethene
- 8.5: Synthesis of Alcohols by Nucleophilic Substitution
- 8.6: Synthesis of Alcohols: Oxidation-Reduction Relation Between Alcohols and Carbonyl Compounds
- 8.7: Organometallic Reagents: Sources of Nucleophilic Carbon for Alcohol Synthesis
- 8.8: Organometallic Reagents in the Synthesis of Alcohols
- 8.9: Keys to Success: An Introduction to Synthetic Strategy
- 9: Further Reactions of Alcohols and the Chemistry of Ethers
- 9.1: Reactions of Alcohols with Base: Preparation of Alkoxides
- 9.2: Reactions of Alcohols with Strong Acids: Alkyloxonium Ions in Substitution and Elimination Reactions of Alcohols
- 9.3: Carbocation Rearrangements
- 9.4: Organic and Inorganic Esters from Alcohols
- 9.5: Names and Physical Properties of Ethers
- 9.6: Williamson Ether Synthesis
- 9.7: Synthesis of Ethers: Alcohols and Mineral Acids
- 9.8: Reactions of Ethers
- 9.9: Reactions of Oxacyclopropanes
- 9.10: Sulfur Analogs of Alcohols and Ethers
- 9.11: Physiological Properties and Uses of Alcohols and Ethers
- 10: Using Nuclear Magnetic Resonance Spectroscopy to Deduce Structure
- 10.1: Physical and Chemical Tests
- 10.2: Defining Spectroscopy
- 10.3: Hydrogen Nuclear Magnetic Resonance
- 10.4: Using NMR Spectra to Analyze Molecular Structure: The Proton Chemical Shift
- 10.5: Tests for Chemical Equivalence
- 10.6: Integration
- 10.7: Spin-Spin Splitting: The Effect of Nonequivalent Neighboring Hydrogens
- 10.8: Spin-Spin Splitting: Some Complications
- 10.9: Carbon-13 Nuclear Magnetic Resonance
- 11: Alkenes: Infrared Spectroscopy and Mass Spectrometry
- 11.1: Naming the Alkenes
- 11.2: Structure and Bonding in Ethene: The Pi Bond
- 11.3: Physical Properties of Alkenes
- 11.4: Nuclear Magnetic Resonance of Alkenes
- 11.5: Catalytic hydrogenatin of Alkenes: Relative Stability of Double Bonds
- 11.6: Preparation of Alkenes from Haloalkanes and Alkyl Sufonates: Bimolecular Elimination Revisited
- 11.7: Preparation of Alkenes by Dehydration of Alcohols
- 11.8: Infrared Spectroscopy
- 11.9: Measuring the Molecular Mass of Organic Compounds: Mass Spectrometry
- 11.10: Fragmentation Patterns of Organic Molecules
- 11.11: Degree of Unsaturation: Another Aid to Identifying Molecular Structure
- 12: Reactions to Alkenes
- 12.1: Why Addition Reactions Proceed: Thermodynamic Feasibility
- 12.2: Catalytic Hydrogenation
- 12.3: Nucleophilic Character of the Pi Bond: Electrophilic Addition of Hydrogen Halides
- 12.4: Alcohol Synthesis by Electrophilic Hydration: Thermodynamic Control
- 12.5: Electrophilic Addition of Halogens to Alkenes
- 12.6: The Generality of Electrophilic Addition
- 12.7: Oxymncuration-Demercuration: A Special Elcctrophilic Addition
- 12.8: Hydroboration-Oxidation: A Stereospecific Anti-Markovnikov Hydration
- 12.9: Diazomethane, Carbenes, and Cyclopropane Synthesis
- 12.10: Oxacyclopropane ( Epoxide) Synthesis: Epoxidation by Peroxycarboxylic Acids
- 12.11: Vicinal SYn Dihydroxylation with Osmium Tetroxide
- 12.12: Oxidative Cleavage: Ozonolysis
- 12.13: Radical Additions: Anti-Markovnikov Product Formation
- 12.14: Dimerization, Oligomerization. and Polymerization of Alkenes
- 12.15: Synthesis of Polymers
- 12.16: Ethene: An Important Industrial Feedstock
- 12.17: Alkenes in Nature - Insect Pheromones
- 13: Alkynes: The Carbon
- 13.1: Naming the Alkynes
- 13.2: Properties and Bonding in the Alkynes
- 13.3: Spectroscopy of the Alkynes
- 13.4: Preparation of Alkynes by Double Elimination
- 13.5: Preparation of Alkynes from Alkynyl Anions
- 13.6: Reduction of Alkynes: The Relative Reactivity of the Two \(\pi\) Bonds
- 13.7: Electrophilic Addition Reactions of Alkynes
- 13.8: Anti-Markovnikov Additions to Triple Bonds
- 13.9: Chemistry of Alkenyl Halides
- 13.10: Ethyne as an Industrial Starting Material
- 13.11: Naturally Occurring and Physiologically Active Alkynes
- 14: Delocalized Pi Systems: Investigation by Ultraviolet and Visible Spectroscopy
- 14.1: Overlap of Three Adjacent p Orbitals: Electron Delocalization in the 2-Propenyl (Allyl) System
- 14.2: Radical Allylic Halogenation
- 14.3: Nucleophilic Substitution of Allylic Halides: SN1 and SN2
- 14.4: Allylic Organometallic Reagents: Useful Three-Carbon Nucleophiles
- 14.5: Two Neighboring Double Bonds: Conjugated Dienes
- 14.6: Electrophilic Attack on Conjugated Dienes: Kinetic and Thermodynamic Control
- 14.7: Delocalization among More than Two Pi Bonds: Extended Conjugation and Benzene
- 14.8: A Special Transformation of Conjugated Dienes: Diels-Alder Cycloaddition
- 14.9: Electrocyclic Reactions
- 14.10: Polymerization of Conjugated Dienes: Rubber
- 14.11: Electronic Spectra: Ultraviolet and Visible Spectroscopy
- 15: Benzene and Aromaticity: Electrophilic Aromatic Substitution
- 1: Structure and Bonding in Organic Molecules