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.
| Alkanes | ||
|---|---|---|
| Free radical chlorination [hν, Cl2] | Free radical bromination [hν, Br2] | Allylic bromination [NBS] |
| Alkenes | ||
| Addition of HCl | Addition of HBr | Addition 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] |
| Hydroboration | Epoxidation [RCO3H] | Dihydroxylation [OsO4] |
| Dihydroxylation [KMnO4] | Cyclopropanation | Dichlorocyclopropanation |
| Ozonolysis (Reductive workup) | Ozonolysis (Oxidative workup) | Oxidative Cleavage [KMnO4] |
| Hydrogenation | Rearrangements (H shift) | Rearrangements (Alkyl shift) |
| Free Radical Addition of HBr | Sharpless Epoxidation |
| Alkynes | ||
|---|---|---|
| Deprotonation (acetylide formation) | SN2 with alkyl halides | Partial reduction (Lindlar) |
| Partial reduction [Na/NH3] | Hydroboration | Oxymercuration |
| Addition of HCl, HBr, or HI (once) | Addition of HCl, HBr, or HI (twice) | Hydrogenation |
| Ozonolysis | Oxidative cleavage [KMnO4] | Alkyne formation via elimination |
| Halogenation [Cl2, Br2, I2] | ||
| Substitution Reactions (SN2) [nucleophile in brackets] | ||
| Alcohol formation [HO(–)] | Alcohol formation [H2O] | Nitrile formation [CN(-)] |
| Thiol formation [HS(–)] | Ether formation [RO(–)] Williamson | Thioether formation [RS( –)] |
| Azides [N3(–)] | Ester formation [RCO2(–)] | Acetylide addition [RC≡C(–)] |
| Alkanes [Gilman reagents] | Alcohol formation [thru ether cleavage] | Ammonium salt formation [RNH2] |
| 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] | |
| Elimination Reactions | ||
|---|---|---|
| E2: Alkenes from alkyl halides | Alkenes from alcohols [strong acid] | Alkenes from alcohols [POCl3] |
| E1: Alkenes from alkyl halides | E1 with rearrangement [alkyl shift] | Hoffmann Elimination |
| Alkyne formation via elimination | E1 with rearrangement [hydride shift] | |
| Reactions of Organometallics | ||
|---|---|---|
| Grignard formation [alkyl halides] | Grignard formation [alkenyl halides] | Reaction of Grignards with acid [H+] |
| Addition of Grignards to aldehydes | Addition of Grignards to ketones | Addition of Grignards to esters |
| Reaction of Grignards with CO2 | Addition of Grignards to nitriles | Formation of organolithium reagents |
| Formation of Gilman reagents | SN2 with Gilman reagents | Addition of Gilman reagents to enones |
| Addition of Gilman to acyl halides | Heck Reaction | Suzuki Reaction |
| Stille Reaction | ||
| 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 |
| Reactions of Alcohols and Thiols | ||
| Deprotonation [alkoxide formation] | Protonation [onium ion formation] | Conversion to ethers [Williamson reaction] |
| Conversion to tosylates/mesylates | Conversion 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 ethers | Thiol formation [SN2] | Thiol oxidation to disulfides |
| Reactions of Dienes | ||
| Diels–Alder reaction | Polymerization of dienes | |
| 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 ketones | Side chain bromination | Nucleophilic Aromatic Substitution (SNAr) |
| Aryne Formation (SNAr via arynes) | ||
| 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 aldehydes | Grignard addition to ketones | Acetal formation [ROH/H+] |
| Acetal hydrolysis [H3O+] | Imine formation [RNH2] | Enamine formation [R2NH] |
| Wolff-Kishner: reduction to alkanes | Clemmensen reduction to alkanes | Oxidation to carboxylic acid [H2CrO4 or KMnO4] |
| Keto-Enol tautomerism | Enolate formation | Aldol addition reaction |
| Alkylation of enolates | Wittig reaction: alkene formation | Thioacetal formation |
| Imine hydrolysis | Oxidation to carboxylic acids [Tollens] | Haloform reaction |
| Baeyer-Villiger Reaction | Aldol Condensation | Cannizarro Reaction |
| Reactions of Carboxylic Acids | ||
| Deprotonation [carboxylate formation] | Formation via Grignard and CO2 | Conversion to acid chloride [SOCl2] |
| Reduction [LiAlH4] | Fischer esterification | Decarboxylation [of β-keto acids] |
| 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 esters | Claisen condensation |
| Transesterification [basic conditions] | ||
| 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] |
| Reactions of α,β-unsaturated ketones [enones] | ||
| Michael reaction [conjugate addition of enolates] | Conjugate addition of Gilman reagents | Conjugate addition of other nucleophiles |
| 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 |
| Reactions of Nitriles | ||
| Addition of Grignard reagents to nitriles | Reduction to amines [LiAlH4] | Hydrolysis to carboxylic acids |
| Miscellaneous | ||
| Robinson annulation | Stork Enamine Reaction | Enamine Hydrolysis |
| Reduction of thioacetals to alkanes [Raney Ni] | Malonic Ester / Acetoacetic Ester Synthesis | Pinacol Rearrangement |
| Hell-Vollhard-Zolinsky Reaction | Wolff Rearrangement | Mannich Reaction |
| Beckmann Rearrangement | Oxidative cleavage of vicinal diols | Kiliani Fischer Synthesis |
THE NEW REACTION GUIDE
Alkanes Alkenes Alkynes Substitution (SN2) Substitution (SN1) Elimination Reactions Reactions of Organometallics Reactions of Epoxides Reactions of Alcohols and Thiols Reactions of Dienes Reactions of Aromatics (Arenes) Reactions of Aldehydes and Ketones Reactions of Carboxylic Acids Reactions of Esters Reactions of Acyl Halides Reactions of α,β-unsaturated ketones [enones] Reactions of Amines and Amides Reactions of Nitriles Miscellaneous
Alkanes
Alkenes
Alkynes
Substitution Reactions (SN2) [nucleophile in brackets]
Substitution Reactions (SN1) [nucleophile in brackets]
Elimination Reactions
Reactions of Organometallics
Reactions of Epoxides
Reactions of Alcohols and Thiols
Reactions of Dienes
Reactions of Aromatics (Arenes)
Reactions of Aldehydes and Ketones
Reactions of Carboxylic Acids
Reactions of Esters
Reactions of Acyl Halides
Reactions of α,β-unsaturated ketones [enones]
Reactions of Amines and Amides
Reactions of Nitriles
Miscellaneous