Organic Chemistry

1. Organic Reaction Mechanisms
   1. Substitution Reactions
      1. Nucleophilic Substitution
         1. SN1 Mechanism
            1. Rate Determining Step
            2. Carbocation Stability and Intermediate Formation
            3. Stereochemical Implications: Racemization
            4. Importance of Solvent: Polar Protic Solvents
            5. Examples and Applications
         2. SN2 Mechanism
            1. Bimolecular Rate Determination
            2. Backside Attack and Inversion of Configuration
            3. Role of Nucleophile Strength and Steric Effects
            4. Solvent Considerations: Polar Aprotic Solvents
            5. Examples and Applications
      2. Electrophilic Substitution
         1. Mechanism in Aromatic Compounds
            1. Electrophile Generation
            2. Formation of Arenium Ion Intermediate
            3. Rearomatization Process
            4. Examples: Halogenation, Nitration, Sulfonation
            5. Directing Effects and Substituent Influence
   2. Elimination Reactions
      1. E1 Mechanism
         1. Unimolecular Rate Determination
         2. Carbocation Formation and Stability
         3. Stereochemistry: Favoring Zaitsev Products
         4. Competing Substitution vs Elimination Pathways
      2. E2 Mechanism
         1. Bimolecular Rate Determination
         2. Antiperiplanar Geometry and Stereoselectivity
         3. Influence of Base Strength and Leaving Group
         4. Regioselectivity: Zaitsev vs Hofmann Products
   3. Addition Reactions
      1. Electrophilic Addition
         1. Mechanism Overview
         2. Importance of Regioselectivity: Markovnikov’s Rule
         3. Anti-Markovnikov Addition through Radical Mechanisms
         4. Stereochemistry and Syn vs Anti Addition
         5. Examples: Hydrohalogenation, Hydration
      2. Nucleophilic Addition
         1. Carbonyl Compound Reactivity
         2. Formation of Tetrahedral Intermediates
         3. Hydride and Grignard Reagents
         4. Stereochemistry: Felkin-Anh Model and Cram’s Rule
   4. Rearrangement Reactions
      1. Carbocation Rearrangements
         1. Hydride Shifts and Alkyl Shifts
         2. Formation of More Stable Carbocations
         3. Examples: Pinacol Rearrangement, Wagner-Meerwein Rearrangement
      2. Sigmatropic Rearrangements
         1. Pericyclic Reaction Characteristics
         2. Cope and Claisen Rearrangements
         3. Woodward-Hoffmann Rules for Predicting Outcomes
   5. Radical Reactions
      1. Mechanism Stages
         1. Initiation: Radical Formation
         2. Propagation: Chain Carriers and Transfer Steps
         3. Termination: Recombination of Radicals
         4. Stability of Radicals: Hyperconjugation and Resonance
         5. Examples: Halogenation of Alkanes, Polymerization Reactions
   6. Pericyclic Reactions
      1. Characteristics of Pericyclic Reactions
         1. Concerted and Stereoselective Processes
         2. Influence of Molecular Orbitals and Frontier Orbital Theory
      2. Cycloaddition
         1. 4+2 Cycloadditions: Diels-Alder Reactions
         2. 2+2 Cycloadditions and Constraints
      3. Sigmatropic Shifts
         1. Definition and Classification (e.g., [1,3]-, [3,3]-Shifts)
         2. Aromatic Transition States
      4. Electrocyclic Reactions
         1. Conrotatory vs. Disrotatory Modes
         2. Stereochemical Outcomes in Electrocyclic Closure and Ring Opening