Organic Reactions
Every reaction you meet in Organic Chemistry I and II — reagents, mechanism, and what the product actually looks like.
Alkene ReactionsAlkyne ReactionsAlkanes & Free RadicalsSubstitution (SN1 & SN2)Elimination (E1 & E2)Alcohol ReactionsEthers & EpoxidesThiols & Sulfur CompoundsAromatic CompoundsAldehydes & KetonesCarboxylic AcidsCarboxylic Acid DerivativesEnols, Enolates & Conjugate AdditionDienes & Pericyclic ReactionsOrganometallic ReagentsRearrangements & Named Reactions
Alkene Reactions (31)
- Acetylide addition [RC≡C(–)]
- Addition of Gilman reagents to enones
- Addition of Gilman to acyl halides
- Addition of Grignard reagents to esters
- Addition of Grignards to aldehydes
- Addition of Grignards to esters
- Addition of Grignards to ketones
- Addition of H3O(+)
- Addition of HBr
- Addition of HCl
- Addition of HCl, HBr, or HI (once)
- Addition of HCl, HBr, or HI (twice)
- Addition of HI
- Bromohydrin formation [Br2/H2O]
- Chlorination [Cl2]
- Cyclopropanation
- Dichlorocyclopropanation
- Dihydroxylation [KMnO4]
- Dihydroxylation [OsO4]
- Ether Formation [H+/ROH]
- Free Radical Addition of HBr
- Hydroboration-oxidation
- Hydrogenation of Alkenes
- Iodination [I2]
- Oxidative Cleavage [KMnO4]
- Oxymercuration [Hg(OAc)2/H2O]
- Oxymercuration [Hg(OAc)2/ROH]
- Ozonolysis (Oxidative workup)
- Ozonolysis (Reductive workup)
- Rearrangements (Alkyl shift)
- Rearrangements (Hydride Shift)
Alkyne Reactions (8)
Alkanes & Free Radicals (3)
Substitution (SN1 & SN2) (15)
- Alcohol formation [ether cleavage]
- Alcohol formation [H2O]
- Alcohol formation [HO(–)]
- Alkanes [Gilman reagents]
- Alkyl chloride formation [HCl]
- Alkyl iodide formation [HI]
- Ammonium salt formation [RNH2]
- Azides [N3(–)]
- Ether formation [ROH]
- Nitrile formation [CN(-)]
- SN1 w/rearrangement [hydride shift]
- SN1 with rearrangement [alkyl shift]
- SN2 with alkyl halides
- SN2 with Gilman reagents
- Thiol formation [SN2]
Elimination (E1 & E2) (7)
Alcohol Reactions (10)
- Conversion to alkyl bromides [PBr3]
- Conversion to alkyl chlorides [SOCl2]
- Conversion to tosylates/mesylates
- Deprotonation [alkoxide formation]
- Oxidation to aldehydes [PCC]
- Oxidation to carboxylic acids [H2CrO4 + others]
- Oxidation to ketones [PCC + others]
- Partial reduction (Lindlar)
- Protection as silyl ethers
- Protonation [onium ion formation]
Ethers & Epoxides (7)
Thiols & Sulfur Compounds (3)
Aromatic Compounds (13)
- Aryne Formation (SNAr via arynes)
- Bromination [Br2 plus catalyst]
- Chlorination [Cl2 plus catalyst]
- Chlorohydrin formation [Cl2/H2O]
- Friedel Crafts acylation [RCOX plus catalyst]
- Friedel Crafts alkylation [R-X plus catalyst]
- Iodination [I2/catalyst]
- Nitration [HNO3/H2SO4]
- Nucleophilic Aromatic Substitution (SNAr)
- Reduction of aromatic ketones
- Reduction of nitro groups
- Side chain bromination
- Sulfonylation [SO3/H2SO4]
Aldehydes & Ketones (26)
- Acetal formation [ROH/H+]
- Acetal hydrolysis [H3O+]
- Aldol addition reaction
- Aldol Condensation
- Alkylation of enolates
- Baeyer-Villiger Reaction
- Cannizzaro Reaction
- Clemmensen reduction to alkanes
- Conversion to ketones [Gilman reagents]
- Cyanohydrin formation [CN(–)]
- Enamine formation [R2NH]
- Enamine Hydrolysis
- Enolate formation
- Halogenation [Cl2, Br2, I2]
- Hydrate formation [H2O]
- Imine formation [RNH2]
- Keto-Enol tautomerism
- Oxidation to carboxylic acid [H2CrO4 or KMnO4]
- Oxidation to carboxylic acids [Tollens]
- Reduction of aldehydes [LiAlH4]
- Reduction of aldehydes [NaBH4]
- Reduction of ketones [LiAlH4]
- Reduction of ketones [NaBH4]
- Thioacetal formation
- Wittig reaction: alkene formation
- Wolff-Kishner: reduction to alkanes
Carboxylic Acids (5)
Carboxylic Acid Derivatives (25)
- Amide Formation from Acid Halides
- Amide Formation Using DCC
- Beckmann Rearrangement
- Claisen condensation
- Conversion to aldehydes [LiAlH(OtBu)3]
- Conversion to amides [RNH2]
- Conversion to anhydrides [RCO2(–)]
- Conversion to esters [ROH]
- Curtius Rearrangement
- Dehydration of amides to nitriles [P2O5]
- Ester formation [RCO2(–)]
- Esterification
- Formation of Diazonium Salts
- Gabriel Synthesis of amines
- Grignard addition to aldehydes
- Hofmann rearrangement
- Hydrolysis to carboxylic acid [acidic]
- Hydrolysis to carboxylic acid [basic]
- Hydrolysis to carboxylic acids
- Reactions of Diazonium Salts
- Reduction to alcohols [LiAlH4]
- Reduction to aldehydes [DIBAL-H]
- Reduction to amines [LiAlH4]
- Reductive Amination
- Transesterification [basic conditions]
Enols, Enolates & Conjugate Addition (2)
Dienes & Pericyclic Reactions (2)
Organometallic Reagents (12)
- Formation of Gilman reagents
- Formation of organolithium reagents
- Formation via Grignard and CO2
- Grignard addition to ketones
- Grignard formation [alkenyl halides]
- Grignard formation [alkyl halides]
- Haloform reaction
- Heck Reaction
- Reaction of Grignards with acid [H+]
- Reaction of Grignards with CO2
- Stille Reaction
- Suzuki Reaction
Rearrangements & Named Reactions (12)
- Alkyl bromide formation [HBr]
- Diels–Alder reaction
- Hell-Vollhard-Zolinsky Reaction
- Kiliani Fischer Synthesis
- Malonic Ester / Acetoacetic Ester Synthesis
- Mannich Reaction
- Oxidative cleavage of vicinal diols
- Pinacol Rearrangement
- Reduction of thioacetals to alkanes [Raney Ni]
- Robinson annulation
- Stork Enamine Reaction
- Wolff Rearrangement