Reactions
Aldol Reaction — Carbonyl Condensation
Complete guide to the aldol reaction: enolate chemistry, C-C bond formation, and α,β-unsaturated carbonyls.
Baeyer-Villiger Oxidation — Ketone to Ester
Complete guide to the Baeyer-Villiger oxidation: peracid oxidation of ketones to esters and lactones.
Claisen Condensation — β-Keto Ester Synthesis
Complete guide to the Claisen condensation: ester enolates, β-keto esters, and acylation reactions.
Clemmensen Reduction — Carbonyl to Methylene
Complete guide to the Clemmensen reduction: zinc amalgam reduction of carbonyls under acidic conditions.
Conjugate Addition (1,4-Addition)
Complete guide to conjugate addition: Michael addition, cuprate addition, and 1,4 vs 1,2 selectivity.
Curtius Rearrangement — Acyl Azide to Isocyanate
Complete guide to the Curtius rearrangement: thermal decomposition of acyl azides to isocyanates.
Diels-Alder Reaction — [4+2] Cycloaddition
Complete guide to the Diels-Alder reaction: pericyclic chemistry, cycloaddition, and ring formation.
E1 Elimination — Unimolecular Elimination
Complete guide to the E1 mechanism: carbocation formation, alkene synthesis, and competition with SN1.
E2 Elimination — Bimolecular Elimination
Complete guide to the E2 mechanism: anti-periplanar geometry, Zaitsev's rule, and alkene formation.
Electrophilic Addition — Alkene Reactions
Complete guide to electrophilic addition: HX addition, halogenation, hydration, and Markovnikov's rule.
Electrophilic Aromatic Substitution (EAS)
Complete guide to EAS: nitration, halogenation, sulfonation, Friedel-Crafts, and directing effects.
Epoxidation — Three-Membered Ether Synthesis
Complete guide to epoxidation: mCPBA epoxidation, Sharpless asymmetric epoxidation, and ring-opening reactions.
Friedel-Crafts Acylation — Acyl Group Introduction
Complete guide to Friedel-Crafts acylation: acyl chlorides, Lewis acid catalysis, and ketone synthesis.
Friedel-Crafts Alkylation — Electrophilic Aromatic Substitution
Complete guide to Friedel-Crafts alkylation: Lewis acid catalysis, carbocation rearrangements, and ring substitution.
Grignard Reaction — Carbon-Carbon Bond Formation
Complete guide to the Grignard reaction: organomagnesium reagents, nucleophilic addition to carbonyls, and synthesis of alcohols.
Heck Reaction — Palladium-Catalyzed Olefination
Complete guide to the Heck reaction: Pd-catalyzed coupling of aryl halides with alkenes.
Hofmann Rearrangement — Amide to Amine
Complete guide to the Hofmann rearrangement: conversion of primary amides to amines with one fewer carbon.
Michael Addition — Conjugate Addition to α,β-Unsaturated Systems
Complete guide to the Michael addition: conjugate addition of nucleophiles to enones and related systems.
Negishi Coupling — Organozinc Cross-Coupling
Complete guide to the Negishi coupling: Pd-catalyzed reaction of organozinc compounds with organic halides.
Nucleophilic Addition — Carbonyl Reactions
Complete guide to nucleophilic addition: Grignard, hydride, cyanide, and Wittig reactions to carbonyls.
SN1 Reaction — Unimolecular Nucleophilic Substitution
Complete guide to the SN1 mechanism: carbocation intermediates, racemization, and solvent effects.
SN2 Reaction — Bimolecular Nucleophilic Substitution
Complete guide to the SN2 mechanism: backside attack, Walden inversion, and stereochemistry.
Sonogashira Coupling — Alkyne-Aryl Bond Formation
Complete guide to the Sonogashira coupling: Pd/Cu-catalyzed reaction of terminal alkynes with aryl halides.
Suzuki Coupling — Palladium-Catalyzed Cross-Coupling
Complete guide to Suzuki coupling: Pd-catalyzed C-C bond formation with organoboron reagents.
Williamson Ether Synthesis — Ether Formation
Complete guide to the Williamson ether synthesis: alkoxide nucleophiles, SN2 reactions, and ether preparation.
Wittig Reaction — Alkene Synthesis from Carbonyls
Complete guide to the Wittig reaction: phosphonium ylides, stereoselectivity, and alkene synthesis.
Wolff-Kishner Reduction — Hydrazone Decomposition
Complete guide to the Wolff-Kishner reduction: hydrazine reduction of carbonyls under basic conditions.