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《有机化学1&2笔记》课程涵盖了有机化学的基础知识和关键反应。 **有机化学1部分（Orgo 1 - Notes）** * **基本概念：** 形式电荷、结构异构体、共振结构、键角与分子形状、凝聚、部分凝聚和路易斯结构、官能团（醇、醚、胺、醛、酮、羧酸、酸酐、酯、酰胺）、有机化合物分类（伯、仲、叔、季）、分子间作用力（氢键、范德华力）。 * **命名与立体化学：** 烷烃和环烷烃的命名与IUPAC系统、纽曼投影、环己烷椅式构象（赤道键与轴向键的能量水平与稳定性）、立体异构体（对映异构体、非对映异构体）、手性中心（手性、R/S构型指定）、顺反异构和内消旋化合物的鉴定。 * **酸碱理论与反应机理：** 酸碱的鉴定（共轭酸、共轭碱）、酸的强度（诱导效应、共振效应）、平衡移动方向、E1、E2、SN1、SN2反应机理、键的断裂（均裂、异裂）、键解离能（活化能、吸热与放热反应）。 * **卤代烷的制备与反应：** 烷烃卤代（溴代或氯代）、单氯代、自由基卤代（引发、链增长、终止）、链增长的能量学。 * **其他官能团的制备与反应：** 有机金属试剂、醇、醚和环氧化物的制备、醇钠的制备与环氧化物的形成、醇的脱水生成烯烃、碳正离子重排、醇转化为卤代烷（HX、SOCl2、PBr3、对甲苯磺酰氯）、环氧化物的反应（酸催化开环、强亲核试剂开环）。 * **加成反应：** 卤化氢加成（离子型、亲电加成）、水合反应（亲电加成）、卤素加成（反式加成）、卤代醇的形成（反式加成）、硼氢化-氧化（顺式加成）、硼氢化-氧化与水合的比较、自由基HBr加成、催化氢化（顺式加成）。 * **氧化反应：** 环氧化、二羟基化、氧化裂解。 * **有机金属试剂（补充）：** 路易斯酸碱、格氏试剂、有机铜试剂、偶联反应。 * **亲核取代反应（补充）：**SN2反应、SN1反应、碳正离子稳定性、根据卤代烷类别和亲核试剂强弱判断SN1或SN2、SN1与SN2的立体化学。 **有机化学2部分（Orgo 2 - Notes）** * **炔烃：** 炔烃的制备、炔烃反应（去质子化乙炔的碱）、酮-烯醇互变异构、硼氢化-氧化、乙炔负离子的反应、炔烃命名。 * **共轭二烯烃：** 共轭二烯烃、电子离域和杂化、共轭二烯烃的稳定性、Diels-Alder反应。 * **芳香性：** 苯及其衍生物的命名、苯的稳定性、芳香杂环的分类、离子芳香化合物和杂环的杂化。 * **亲电芳香取代：** 卤代、取代基对亲电芳香取代的影响、取代苯的定位效应、活化环的反应、亲核芳香取代（加成-消除，消除-加成）。 * **羰基化合物的反应：** 醇的氧化、羰基的还原、保护基、有机铜试剂（吉尔曼试剂）、Simmons-Smith反应、氢化物亲核加成、Suzuki偶联、Heck反应。 * **波谱分析：** 质谱、红外光谱（IR）、核磁共振氢谱（¹H NMR）。 * **含氮有机化合物：** 亚胺的形成、缩醛的形成与水解。 * **羧酸及其衍生物：** 羧酸的制备、羧酸的酸碱反应、羧酸的诱导效应、取代苯甲酸、羧酸衍生物的性质、酰氯命名、亲核酰基取代、酰胺的合成、酸酐的反应、羧酸的酯化（Fischer酯化）、腈的形成、水解（酸/碱催化下的酰胺水解、酸催化下的酯水解、碱催化下的酯水解）、内酯（环状酯）、缩醛的水解。 * **烯醇与α-碳化学：** 烯醇、α-碳的卤代、卤仿反应、直接烯醇烷基化。 * **常见碳负离子反应：** Aldol反应、Claisen反应、丙二酸酯合成法、乙酰乙酸酯合成法、Michael反应。
Orgo 1 - NotesFormal ChargeConstitutional Isomers (aka Structural Isomers)Resonance StructuresBond Angles & Molecular ShapeCondensed, Partially Condensed & Lewis StructuresFunctional Groups (Alcohols; Ethers; Amines; Aldehydes; Ketones; Carboxylic Acids; Anhydrides; Esters; Amides)Organic Compound Classifications (primary; secondary; tertiary; quaternary)Intermolecular Forces (Hydrogen Bonding; Vander Waals Forces)Nomenclature & IUPAC System (Alkanes; Cycloalkanes)Newman ProjectionsCyclohexane Chair Conformations (equatorial vs axial energy levels & stabilization)Stereoisomers, Enantiomers (including Enantiomer Nomenclature) & identifying Diastereomers, Chiral Centers (Chirality) and R & S Assignment, cis vs trans & identifying Meso CompoundsAcids & Bases (identifying the conjugate acid & conjugate base); Acid Strength (Inductive Effect; Resonance Effect); Equilibrium favors formation of...E1, E2, SN1, SN2 ReactionsBond Breaking (Homolitic & Heterolitic cleavage - Homolysis & Heterolysis)Bond Dissociation Energy (BDE) (Activation Energy; Endothermic & Exothermic Reactions)Preparation of Haloalkanes by Halogenation of Alkanes (Br or Cl)Monochlorination (Halogenation)Radical Halogenation (Initiation, Propagation #1, Propagation #2, Termination)Energetics of Chain PropagationPreparation of Haloalkanes by Halogenation of AlkanesHalogenation (Bromination vs Chlorination)Organometallic ReagentsPreparation of Alcohols, Ethers, and EpoxidesPreparation of Alkoxides & Forming Epoxides from HalohydrinsDehydration of Alcohols to AlkenesCarbocation RearrangementsConversion of Alcohols to Alkyl Halides with HXConversion of Alcohols to Alkyl Halides with SOCl2 & PBr3Conversion of Alcohols to Alkyl TosylatesEpoxide Reactions with AcidsOpening Epoxide Ring with Strong NucleophileHydrohalogenation - Ionic & Electrophilic Addition of HXHydration - Electrophilic Addition of WaterHalogenation (Anti Addition)Halogenation - Electrophilic AdditionHalohydrin Formation (Anti Addition)Hydroboration-Oxidation (SYN Addition)Hydroboration-Oxidation vs HydrationRadical Addition of HBRCatalytic Hydrogenation (SYN Addition)Epoxidation (Oxidation Reaction)Dihydroxylation (Oxidation Reaction)Oxidative Cleavage (Oxidation Reaction)Lewis Acids & BasesGrignard ReagentsOrganometallic ReagentsCoupling Reactions of OrganocupratesOrganocupratesAlkyl Halide NomenclatureSN2 Reactions (Nucleophilic Substitution)SN1 Reactions (Nucleophilic Substitution)Carbocation StabilityDetermining SN1 or SN2 based on Alkyl Halide Class & Strong/Weak NucleophileSN1 & SN2 StereochemistryOrgo 2 - NotesPreparation of AlkynesAlkyne Rxns - Bases that can Deprotonate AcetyleneKeto-Enol TautomerizationHydroboration-OxidationKeto-Enol Tautomerization & Hydroboration-OxidationAcetylide Anion RxnsAlkyne NomenclatureConjugate DienesElectron Delocalization & HybridizationStability of Conjugate DienesDiels-Alder Rxn (Rules 1-4)Nomenclature of Benzene DerivativesStability of BenzeneClassifying Aromatic HeterocyclesIonic Aromatic Compounds & Heterocycle HybridizationHalogenationSubstituent Effects on Electrophilic Aromatic SubstitutionOrientation Effects of Substituted BenzenesRxns of Activated RingsNucleophilic Aromatic Substitution - Addition-EliminationNucleophilic Aromatic Substitution - Elimination-AdditionOxidation of AlcoholCarbonyl ReductionProtecting GroupsOrganocuprates (Gilman Reagents)Simmons-Smith RxnNucleophilic Addition of HydrideSuzuki MechanismHeck RxnMass SpectrometryIR StructureProton NMRImine FormationAcetal FormationAcetal HydrolysisPreparation of Carboxylic AcidsAcid-Base Rxns of Carboxylic AcidsCarboxylic Acid Inductive EffectsSubstituted Benzoic AcidsProperties of Carboxylic Acid DerivativesAcid Chloride NomenclatureNucleophilic Acyl SubstitutionAmide SynthesisAnhydride RxnCarboxylic Acid - Fischer EsterificationNitrile FormationHydrolysis (Amide Hydrolysis in Acid, Ester-Acid Hydrolysis, Ester-Base Hydrolysis)Esters - Lactone (Cyclic Ester)Hydrolysis of AcetalsCarboxylic Acid - Acid Base RxnsNomenclature of Carboxylic Acid DerivativesFischer Esterification - Carboxylic AcidEnolateHalogenation at Alpha CarbonHaloform RxnDirect Enolate AlkylationAldol RxnClaisen RxnMalonic Ester RxnAcetoacetic Ester RxnMichael Rxn
