Description
Taylor & Francis Inc Organic Chemistry An Acid-Base Approach 2011 Edition by Michael B. Smith
Based on the premise that many, if not most, reactions in organic chemistry can be explained by variations of fundamental acid-base concepts, Organic Chemistry: An Acid-Base Approach provides a framework for understanding the subject that goes beyond mere memorization. The individual steps in many important mechanisms rely on acid-base reactions, and the ability to see these relationships makes understanding organic chemistry easier. Using several techniques to develop a relational understanding, this textbook helps students fully grasp the essential concepts at the root of organic chemistry.Providing a practical learning experience with numerous opportunities for self-testing, the book contains:Checklists of what students need to know before they begin to study a topicChecklists of concepts to be fully understood before moving to the next subject areaHomework problems directly tied to each concept at the end of each chapterEmbedded problems with answers throughout the materialExperimental details and mechanisms for key reactionsThe reactions and mechanisms contained in the book describe the most fundamental concepts that are used in industry, biological chemistry and biochemistry, molecular biology, and pharmacy. The concepts presented constitute the fundamental basis of life processes, making them critical to the study of medicine. Reflecting this emphasis, most chapters end with a brief section that describes biological applications for each concept. This text provides students with the skills to proceed to the next level of study, offering a fundamental understanding of acids and bases applied to organic transformations and organic molecules. Table of contents : - IntroductionA Brief History of Organic ChemistryThe Variety and Beauty of Organic MoleculesWhy Is an Acid-BaseTheme Important?Acids and Bases in General ChemistryAcids and Bases in Organic ChemistryHow Are the Two Acid-Base Definitions Related?Acid and Base StrengthLewis Acids and Lewis BasesWhy Is Acid-Base Chemistry a Theme for Organic Chemistry?Biological RelevanceBondingThe ElementsWhat Is a Chemical Bond? Ionic versus CovalentThe Covalent Carbon-Carbon BondMolecular OrbitalsTetrahedral Carbons and sp3 HybridizationHow Strong Is a Covalent Bond? Bond Dissociation EnergyPolarized Covalent -BondsBiological RelevanceAlkanes, Isomers, and an Introduction to NomenclatureThe Fundamental Structure of Alkanes Based on the sp3 Hybrid ModelMillions of Hydrocarbons: AlkanesCombustion Analysis and Empirical FormulasThe Acid or Base Properties of AlkanesIsomersNaming Millions of Isomers: Rules of Nomenclature. The IUPAC Rules of NomenclatureRings Made of Carbon. Cyclic CompoundsBiological RelevanceFunctional GroupsIntroducing a Functional Group: AlkenesAnother Hydrocarbon Functional Group: AlkynesHydrocarbons with Several Multiple BondsReactivity of Polarized Covalent -BondsFormal ChargeHeteroatom Functional GroupsAcid-Base Properties of Functional GroupsPolarity and Intermolecular ForcesFunctional Groups with Polarized -BondsBenzene: A Special Cyclic HydrocarbonBiological RelevanceAcids, Bases, Nucleophiles, and ElectrophilesAcid-Base EquilibriaPolarized Hydrogen-Heteroatom Bonds: Acidic UnitsFactors That Influence the Strength of a Bronsted-Lowry AcidOrganic BasesLewis Acids and Lewis BasesA Positive Carbon Atom Can Accept ElectronsNucleophilesBiological RelevanceChemical Reactions, Bond Energy, and KineticsA Chemical ReactionBond Dissociation Enthalpy and ReactionsTransition StatesReactive IntermediatesFree Energy. Influence of Enthalpy and EntropyEnergetics. Starting Materials, Transition States, Intermediates, and Products on a Reaction CurveCompeting ReactionsMechanismsWhy Does a Chemical Reaction Occur? Defining a "Reactive" CenterReversible Chemical ReactionsKineticsNo ReactionBiological RelevanceRotamers and ConformationRotamersLonger Chain Alkanes: Increased Torsional StrainConformations of Alkenes and Alkynes: Introducing -BondsInfluence of Heteroatoms on the Rotamer PopulationCyclic AlkanesSubstituted CyclohexanesLarger RingsCyclic AlkenesIntroducing Heteroatoms into a RingBiological RelevanceStereoisomers: Chirality, Enantiomers, and DiastereomersStereogenic Carbons and StereoisomersSpecific Rotation: A Physical PropertyAbsolute Configuration (R and S Nomenclature)AlkenesDiastereomersStereogenic Centers in Cyclic MoleculesStereogenic Centers in Complex MoleculesOptical ResolutionBiological RelevanceAcid-Base Reactions of -BondsAlkenes and Acid-Base ChemistryCarbocation IntermediatesAlkenes React with Weak Acids in the Presence of an Acid CatalystAlkenes React as Lewis BasesAlkenes React as Lewis Bases with Electrophilic Oxygen. Oxidation of Alkenes to OxiranesAlkynes React as Bronsted-Lowry Bases or Lewis BasesReactions That Are Not Formally Acid-Base ReactionsNon-ionic Reactions: Radical Intermediates and Alkene PolymerizationSynthetic TransformationsBiological RelevanceNucleophiles: Lewis Base-Like Reactions at sp3 CarbonAlkyl Halides, Sulfonate Esters, and the Electrophilic C-X BondNucleophiles and Bimolecular Substitution (the SN2 Reaction)Functional Group Transformations via the SN2 ReactionA Tertiary Halide Reacts with a Nucleophile When the Solvent Is WaterCarbocation RearrangementsSolvolysis Reactions of Alkyl HalidesPreparation of Halides and Sulfonate Esters by Substitution ReactionsReactions of EthersFree Radical Halogenation of AlkanesApplications to SynthesisBiological RelevanceBase-Induced Elimination ReactionsBimolecular EliminationStereochemical Consequences of the E2 ReactionThe E2 Reaction in Cyclic MoleculesUnimolecular EliminationIntramolecular Elimination1,3 Elimination: DecarboxylationElimination Reactions of Vinyl Halides: Formation of AlkynesElimination Functional Group ExchangesBiological RelevanceSubstitution and Elimination Reactions Can CompeteA Few Simplifying AssumptionsProtic versus Aprotic and WaterNucleophilic Strength versus Base StrengthThe Nature of the HalideWhat about Secondary Halides?Strength and Limitations of the Simplifying AssumptionsWhen Do the Assumptions Fail?Spectroscopic Methods of IdentificationLight and EnergyMass SpectrometryInfrared SpectroscopyNuclear Magnetic Resonance SpectroscopyThe Structure of an Unknown Molecule May Be DeterminedCarbon-13 NMR Spectroscopy: Counting the CarbonsBiological RelevanceOrganometallic ReagentsIntroducing Magnesium into a MoleculeReaction of Aryl and Vinyl Halides with MagnesiumGrignard Reagents Are BasesGrignard Reagents Are Poor Nucleophiles with Alkyl HalidesOrganolithium ReagentsOrganocupratesOrganometallic DisconnectionsBiological RelevanceCarbonyl Compounds: Structure, Nomenclature, ReactivityThe Carbonyl GroupAldehydes and Ketones. NomenclatureChemical Reactivity of Ketones and AldehydesCarboxylic Acids. Nomenclature and PropertiesDicarboxylic AcidsDicarboxylic Acids Have Two pKa ValuesCarboxylic Acid Derivatives. Nomenclature and PropertiesAcyl Substitution with Carboxylic Acid DerivativesSulfonic AcidsBiological RelevanceOxidationDefining an OxidationOxidation of Alcohols with Chromium(VI)Oxidation of AlkenesOxidative CleavageSummary of Functional Group ExchangesBiological RelevanceReactions of Aldehydes and KetonesChemical Reactivity of the Carbonyl GroupReversible versus Irreversible Acyl AdditionReaction of Aldehydes or Ketones with Strong NucleophilesOrganometallic Reagents Are NucleophilesWater: A Weak Nucleophile That Gives Reversible Acyl AdditionAlcohols: Neutral Nucleophiles That Give Reactive ProductsAmines Are Nucleophiles That React to Give Imines or EnaminesCarbon-Carbon Bond-Forming Reactions and Functional Group ModificationBiological RelevanceReductionDefining a ReductionHydrides as Reducing AgentsCatalytic HydrogenationDissolving Metal ReductionsSummary of Functional Group ExchangesBiological RelevanceCarboxylic Acid Derivatives and Acyl SubstitutionChemical Reactivity of Carboxylic Acid DerivativesAcyl Substitution. Acid Derivatives React with Water: HydrolysisPreparation of Acid ChloridesPreparation of Acid AnhydridesPreparation of EstersAmidesThe Reaction of Carboxylic Acid Derivatives with Carbon NucleophilesReaction of Organometallics with Other Electrophilic "Carbonyl" MoleculesDicarboxylic Acid DerivativesBaeyer-Villiger OxidationSulfonic Acid DerivativesSulfate Esters and Phosphate EstersNitriles Are Carboxylic Acid DerivativesCarbon-Carbon Bond-Forming Reactions and Functional Group Exchanges of Acid DerivativesBiological RelevanceAromatic Compounds and Benzene DerivativesBenzene and AromaticityFunctionalized Benzene Derivatives and a New Nomenclature SystemElectrophilic Aromatic SubstitutionDisubstituted Benzene DerivativesPolysubstituted Benzene DerivativesReduction of Aromatic CompoundsAromaticity in Monocyclic Molecules Other Than BenzenePolynuclear Aromatic HydrocarbonsAromatic Amines and Diazonium SaltsNucleophilic Aromatic SubstitutionAromatic Disconnections and Functional Group Exchange ReactionsSynthesis of Aromatic CompoundsBiological RelevanceEnolate Anions: Acyl Addition and Acyl SubstitutionAldehydes and Ketones Are Weak AcidsEnolate Anions Are Nucleophiles. The Aldol CondensationNon-nucleophilic BasesEnolate Anions from Unsymmetrical KetonesDehydration of Aldol ProductsThe Intramolecular Aldol CondensationEster EnolatesDecarboxylationEnolate AlkylationPhosphorus Ylids and the Wittig ReactionMany New Synthetic PossibilitiesBiological RelevanceDifunctional Molecules: Dienes and Conjugated Carbonyl CompoundsConjugated DienesConjugated Carbonyl CompoundsDetecting Conjugation: Ultraviolet SpectroscopyReactions of Conjugated -BondsPolymers from Conjugated MoleculesSynthetic PossibilitiesBiological RelevanceDifunctional Molecules: Pericyclic ReactionsFrontier Molecular Orbitals: HOMOs and LUMOsReactivity of Dienes and AlkenesSelectivitySigmatropic RearrangementsReview of Synthetic TransformationsBiological RelevanceDisconnections and SynthesisWhat Is Synthesis?Specifying a Starting Material for a Given TargetThe Starting Material Is UnknownDisconnection of Molecules with Problematic Structural FeaturesHeteroaromatic CompoundsNitrogen in an Aromatic RingOxygen and Sulfur in an Aromatic RingSubstitution Reactions in Heterocyclic Aromatic CompoundsReduced Forms of HeterocyclesHeteroaromatic Compounds with More Than One RingAromatic Substitution Reactions of Polycyclic HeterocyclesSynthesis of HeterocyclesBiological RelevanceMultifunctional Compounds: Amino Acids and PeptidesA Review of Reactions That Form AminesReactions of AminesDifunctional Molecules: Amino AcidsBiological Relevance. Peptides Are Polyamides of Amino Acid ResiduesBiological Relevance. Proteins and Enzymes Are PolypeptidesNew Synthetic MethodologyMultifunctional Compounds: CarbohydratesPolyhydroxy Carbonyl CompoundsBiological Relevance. Oligosaccharides and PolysaccharidesReactions of CarbohydratesSynthesis of CarbohydratesBiological Relevance. Nucleosides and Nucleotides (Heterocycles Combined with Sugars)Biological Relevance. PolynucleotidesSynthesis of PolynucleotidesIndexshow more