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DAT Prep/Organic Chemistry/Chemical Synthesis

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Nucleophilic Substitution

The SN2 Reaction The SN1 Reaction Leaving Groups and Nucleophiles

Elimination

The E2 Reaction The E1 Reaction Elimination Orientation

Choosing the Pathway

Substrate and Reagent Analysis Solvent Effects and the Full Decision

Reactions of Alkenes

Hydrohalogenation Acid-Catalyzed Hydration Oxymercuration and Alkoxymercuration Halogenation and Halohydrin Formation Hydroboration-Oxidation Radical Hydrobromination Epoxidation Syn Dihydroxylation Ozonolysis Catalytic Hydrogenation of Alkenes

Reactions of Alkynes

Additions to Alkynes Alkyne Hydration Alkyne Reductions Acetylide Chemistry Alkyne Synthesis by Double Elimination

Reactions of Alcohols

Alcohols to Alkyl Halides Alcohol Dehydration Alcohol Oxidation

Reactions of Ethers and Epoxides

Ether Synthesis Ether Cleavage Epoxide Opening

Radical Halogenation

Alkane Halogenation Allylic and Benzylic Bromination

Reactions of Aromatics

Electrophilic Aromatic Substitution Friedel-Crafts Reactions Directing Effects Aromatic Side-Chain Reactions Diazonium Chemistry

Reactions of Ketones and Aldehydes

Nucleophilic Addition to Carbonyls Acetals and Protecting Groups Imines and Enamines Hydride Reduction of Carbonyls Grignard and Organolithium Addition The Wittig Reaction Conjugate Addition

Reactions of Carboxylic Acids and Derivatives

The Acyl Substitution Framework Esters: Formation and Hydrolysis Acid Chlorides Reductions of Acid Derivatives Grignard Reagents with Esters Amides and the Hofmann Rearrangement Nitriles

Alpha-Carbon Chemistry

Enols and Enolates Kinetic and Thermodynamic Enolates Alpha-Halogenation and the Haloform Reaction The Aldol Reaction The Claisen Condensation Decarboxylation and Ester Syntheses

Synthesis Planning

Two-Step Synthesis Protecting Groups and Reaction Order Retrosynthetic Analysis Carbon-Skeleton Construction Chemoselectivity Selective Reagents in Polyfunctional Molecules

Topics

Nucleophilic Addition to Carbonyls Acetals and Protecting Groups Imines and Enamines Hydride Reduction of Carbonyls Grignard and Organolithium Addition The Wittig Reaction Conjugate Addition

Reactions of Ketones and Aldehydes

Grignard and Organolithium Addition

Summary

Practice Questions

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