Master Organic Chemistry Reaction Guide

Reaction Guide

The Reaction Guide gives individual descriptions, examples, and mechanisms of more than 185 of the most common reactions encountered in undergraduate organic chemistry. Only members can access all of the full pages.  Reactions highlighted in red are open-access.

AlkanesAlkenesAlkynesSubstitution (SN2)Substitution (SN1)
Elimination ReactionsAlcohols and ThiolsOrganometallicsEpoxidesDienes
Aromatics (Arenes)Aldehydes and KetonesCarboxylic AcidsEstersAcyl Halides 
α,β-unsaturated alkenes
Amides Nitriles Miscellaneous


Alkanes
Free radical chlorination [hν, Cl2]Free radical bromination [hν, Br2]Allylic bromination [NBS]

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Alkenes
Addition of HClAddition of HBrAddition of HI
Addition of H3O(+)Chlorination [Cl2]Bromination [Br2]
Iodination [I2]Chlorohydrin formation [Cl2/H2O]Bromohydrin formation [Br2/H2O]
Ether Formation [H+/ROH]Oxymercuration [Hg(OAc)2/H2O]Oxymercuration [Hg(OAc)2/ROH]
HydroborationEpoxidation [RCO3H]Dihydroxylation [OsO4]
Dihydroxylation [KMnO4]CyclopropanationDichlorocyclopropanation
Ozonolysis (Reductive workup)Ozonolysis (Oxidative workup)Oxidative Cleavage [KMnO4]
 HydrogenationRearrangements (H shift)Rearrangements (Alkyl shift)
Free Radical Addition of HBrSharpless Epoxidation

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Alkynes
Deprotonation (acetylide formation)SN2 with alkyl halidesPartial reduction (Lindlar)
Partial reduction [Na/NH3]HydroborationOxymercuration
Addition of HCl, HBr, or HI (once)Addition of HCl, HBr, or HI (twice)Hydrogenation
OzonolysisOxidative cleavage [KMnO4]Alkyne formation via elimination
Halogenation [Cl2, Br2, I2]

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Substitution Reactions (SN2) [nucleophile in brackets]
Alcohol formation [HO(–)]Alcohol formation [H2O]Nitrile formation [CN(-)]
Thiol formation [HS(–)]Ether formation [RO(–)] WilliamsonThioether formation [RS(–)]
Azides [N3(–)]Ester formation [RCO2(–)]Acetylide addition [RC≡C(–)]
Alkanes [Gilman reagents]Alcohol formation [thru ether cleavage]Ammonium salt formation [RNH2]

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Substitution Reactions (SN1) [nucleophile in brackets]
Alcohol formation [H2O]Ether formation [ROH]Alcohol formation [ether cleavage]
Alkyl chloride formation [HCl]Alkyl bromide formation [HBr]Alkyl iodide formation [HI]
SN1 w/ rearrangement [alkyl shift] SN1 w/rearrangement [hydride shift]

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Elimination Reactions
E2: Alkenes from alkyl halidesAlkenes from alcohols [strong acid]Alkenes from alcohols [POCl3]
E1: Alkenes from alkyl halidesE1 with rearrangement [alkyl shift]Hoffmann Elimination
Alkyne formation via elimination E1 with rearrangement [hydride shift]

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Reactions of Organometallics
Grignard formation [alkyl halides]Grignard formation [alkenyl halides]Reaction of Grignards with acid [H+]
Addition of Grignards to aldehydesAddition of Grignards to ketonesAddition of Grignards to esters
Reaction of Grignards with CO2Addition of Grignards to nitrilesFormation of organolithium reagents
Formation of Gilman reagentsSN2 with Gilman reagentsAddition of Gilman reagents to enones
Addition of Gilman to acyl halidesHeck Reaction Suzuki Reaction
Stille Reaction

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Reactions of Epoxides
Epoxide opening [basic conditions]Epoxide opening [acidic conditions]Epoxide opening [diol formation]
Epoxide formation [from halohydrins]Epoxide formation [from alkenes]Sharpless Epoxidation of alkenes

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Reactions of Alcohols and Thiols
Deprotonation [alkoxide formation]Protonation [onium ion formation]Conversion to ethers [Williamson reaction]
Conversion to tosylates/mesylatesConversion to alkyl chlorides [SOCl2]Conversion to alkyl bromides [PBr3]
Oxidation to aldehydes [PCC]Oxidation to ketones [PCC + others]Oxidation to carboxylic acids [H2CrO4 + others]
Protection as silyl ethersThiol formation [SN2]Thiol oxidation to disulfides

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Reactions of Dienes
Diels–Alder reactionPolymerization of dienes

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Reactions of Aromatics (Arenes)
Nitration [HNO3/H2SO4]Chlorination [Cl2 plus catalyst]Bromination [Br2 plus catalyst]
Sulfonylation [SO3/H2SO4]Friedel Crafts alkylation [R-X plus catalyst]Friedel Crafts acylation [RCOX plus catalyst]
Iodination [I2/catalyst]Side chain oxidation [KMnO4]Reduction of nitro groups
Reduction of aromatic ketonesSide chain bromination  Nucleophilic Aromatic Substitution (SNAr)
Aryne Formation (SNAr via arynes)

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Reactions of Aldehydes and Ketones
Hydrate formation [H2O]Cyanohydrin formation [CN(–)]Reduction of aldehydes [NaBH4]
Reduction of aldehydes [LiAlH4]Reduction of ketones [NaBH4]Reduction of ketones [LiAlH4]
Grignard addition to aldehydesGrignard addition to ketonesAcetal formation [ROH/H+]
Acetal hydrolysis [H3O+]Imine formation [RNH2]Enamine formation [R2NH]
Wolff-Kishner: reduction to alkanesClemmensen reduction to alkanesOxidation to carboxylic acid [H2CrOor KMnO4]
Keto-Enol tautomerismEnolate formationAldol addition reaction
Alkylation of enolatesWittig reaction: alkene formationThioacetal formation
Imine hydrolysisOxidation to carboxylic acids [Tollens]Haloform reaction
Baeyer-Villiger Reaction Aldol Condensation Cannizarro Reaction

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Reactions of Carboxylic Acids
Deprotonation [carboxylate formation]Formation via Grignard and CO2Conversion to acid chloride [SOCl2]
Reduction [LiAlH4]Fischer esterificationDecarboxylation [of β-keto acids]

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Reactions of Esters
Reduction to aldehydes [DIBAL-H]Reduction to alcohols [LiAlH4]Hydrolysis to carboxylic acid [acidic]
Hydrolysis to carboxylic acid [basic]Addition of Grignard reagents to estersClaisen condensation
Transesterification [basic conditions]

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Reactions of  Acyl  Halides
Conversion to esters [ROH]Conversion to carboxylic acids [H2O]Conversion to anhydrides [RCO2(–)]
Conversion to amides [RNH2]Conversion to ketones [Gilman reagents]Conversion to aldehydes [LiAlH(OtBu)3]

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Reactions of α,β-unsaturated ketones [enones]
Michael reaction [conjugate addition of enolates]Conjugate addition of Gilman reagentsConjugate addition of other nucleophiles

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Reactions of Amines and Amides
Dehydration of amides to nitriles [P2O5]Hofmann rearrangement Gabriel Synthesis of amines
Reductive Amination Formation of Diazonium Salts Reactions of Diazonium Salts
Amide Formation Using DCC Amide Formation from Acid Halides Curtius Rearrangement

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Reactions of Nitriles
Addition of Grignard reagents to nitrilesReduction to amines [LiAlH4]Hydrolysis to carboxylic acids

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Miscellaneous
Robinson annulationStork Enamine ReactionEnamine Hydrolysis
Reduction of thioacetals to alkanes [Raney Ni]Malonic Ester / Acetoacetic Ester Synthesis  Pinacol Rearrangement
Hell-Vollhard-Zolinsky Reaction Wolff Rearrangement Mannich Reaction
Beckmann RearrangementOxidative cleavage of vicinal diolsKiliani Fischer Synthesis

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THE NEW REACTION GUIDE

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