Free radical chlorination [hν, Cl2]

Free radical bromination [hν, Br2]

Allylic bromination [NBS]

Addition of HCl

Addition of H3O(+)

Iodination [I2]

Ether Formation [H+/ROH]

Dihydroxylation [KMnO4]

Ozonolysis (Reductive workup)

 Hydrogenation of Alkenes

Free Radical Addition of HBr

Addition of HBr

Chlorination [Cl2]

Chlorohydrin formation [Cl2/H2O]

Oxymercuration [Hg(OAc)2/H2O]

Epoxidation [RCO3H]


Ozonolysis (Oxidative workup)

Rearrangements (H shift)

Sharpless Epoxidation

Addition of HI

Bromohydrin formation [Br2/H2O]

Oxymercuration [Hg(OAc)2/ROH]

Dihydroxylation [OsO4]


Oxidative Cleavage [KMnO4]

Rearrangements (Alkyl shift)

Deprotonation (acetylide formation)

Partial reduction [Na/NH3]

Addition of HCl, HBr, or HI (once)


Halogenation [Cl2, Br2, I2]

SN2 with alkyl halides


Addition of HCl, HBr, or HI (twice)

Oxidative cleavage [KMnO4]

Partial reduction (Lindlar)


Hydrogenation of Alkynes

Alkyne formation via elimination

Alcohol formation [HO(–)]

Thiol formation [HS(–)]

Azides [N3(–)]

Alkanes [Gilman reagents]

Alcohol formation [H2O]

Ester formation [RCO2(–)]

Nitrile formation [CN(-)]

Thioether formation [RS(–)]

Acetylide addition [RC≡C(–)]

Ammonium salt formation [RNH2]

Alcohol formation [H2O]

Alkyl chloride formation [HCl]

SN1 w/ rearrangement [alkyl shift]

Ether formation [ROH]

Alkyl bromide formation [HBr]

SN1 w/rearrangement [hydride shift]

Alcohol formation [ether cleavage]

Alkyl iodide formation [HI]

E2: Alkenes from alkyl halides

E1: Alkenes from alkyl halides

Alkyne formation via elimination

Alkenes from alcohols [strong acid]

E1 with rearrangement [hydride shift]

Alkenes from alcohols [POCl3]

Hofmann Elimination

Grignard formation [alkyl halides]

Addition of Grignards to aldehydes

Reaction of Grignards with CO2

Formation of Gilman reagents

Addition of Gilman to acyl halides

Stille Reaction

Grignard formation [alkenyl halides]

Addition of Grignards to ketones

SN2 with Gilman reagents

Heck Reaction

Reaction of Grignards with acid [H+]

Addition of Grignards to esters

Formation of organolithium reagents

Addition of Gilman reagents to enones

 Suzuki Reaction

Epoxide opening [basic conditions]

Epoxide formation [from halohydrins]

Epoxide opening [acidic conditions]

Epoxide formation [from alkenes]

Epoxide opening [diol formation]

Sharpless Epoxidation of alkenes

Deprotonation [alkoxide formation]

Conversion to tosylates/mesylates

Oxidation to aldehydes [PCC]

Protection as silyl ethers

Protonation [onium ion formation]

Conversion to alkyl chlorides [SOCl2]

Oxidation to ketones [PCC + others]

Thiol formation [SN2]

Conversion to alkyl bromides [PBr3]

Oxidation to carboxylic acids [H2CrO4 + others]

Thiol oxidation to disulfides

Diels–Alder reaction

Polymerization of dienes

Nitration [HNO3/H2SO4]

Sulfonylation [SO3/H2SO4]

Iodination [I2/catalyst]

Reduction of aromatic ketones

Aryne Formation (SNAr via arynes)

Chlorination [Cl2 plus catalyst]

Friedel Crafts alkylation [R-X plus catalyst]

Side chain bromination

Bromination [Br2 plus catalyst]

Friedel Crafts acylation [RCOX plus catalyst]

Reduction of nitro groups

Nucleophilic Aromatic Substitution (SNAr)

Hydrate formation [H2O]

Reduction of aldehydes [LiAlH4]

Grignard addition to aldehydes

Acetal hydrolysis [H3O+]

Wolff-Kishner: reduction to alkanes

Keto-Enol tautomerism

Alkylation of enolates

Baeyer-Villiger Reaction

Cyanohydrin formation [CN(–)]

Reduction of ketones [NaBH4]

Grignard addition to ketones

Imine formation [RNH2]

Clemmensen reduction to alkanes

Enolate formation

Wittig reaction: alkene formation

Oxidation to carboxylic acids [Tollens]

Aldol Condensation

Reduction of aldehydes [NaBH4]

Reduction of ketones [LiAlH4]

Acetal formation [ROH/H+]

Enamine formation [R2NH]

Oxidation to carboxylic acid [H2CrO4 or KMnO4]

Aldol addition reaction

Thioacetal formation

Haloform reaction

Cannizzaro Reaction

Deprotonation [carboxylate formation]

Reduction [LiAlH4]

Formation via Grignard and CO2

Conversion to acid chloride [SOCl2]

Decarboxylation [of β-keto acids]

Reduction to aldehydes [DIBAL-H]

Hydrolysis to carboxylic acid [basic]

Transesterification [basic conditions]

Reduction to alcohols [LiAlH4]

Addition of Grignard reagents to esters

Hydrolysis to carboxylic acid [acidic]

Claisen condensation

Conversion to esters [ROH]

Conversion to amides [RNH2]

Conversion to carboxylic acids [H2O]

Conversion to ketones [Gilman reagents]

Conversion to anhydrides [RCO2(–)]

Conversion to aldehydes [LiAlH(OtBu)3]

Conjugate addition of Gilman reagents

Conjugate addition of other nucleophiles

Dehydration of amides to nitriles [P2O5]

Reductive Amination

Amide Formation Using DCC

Hofmann rearrangement

Formation of Diazonium Salts

Amide Formation from Acid Halides

Gabriel Synthesis of amines

Reactions of Diazonium Salts

 Curtius Rearrangement

Reduction to amines [LiAlH4]

Hydrolysis to carboxylic acids

Robinson annulation

Reduction of thioacetals to alkanes [Raney Ni]

Hell-Vollhard-Zolinsky Reaction

Beckmann Rearrangement

Stork Enamine Reaction

Malonic Ester / Acetoacetic Ester Synthesis 

Wolff Rearrangement

Oxidative cleavage of vicinal diols

Enamine Hydrolysis

Pinacol Rearrangement

Mannich Reaction

Kiliani Fischer Synthesis