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by James

The Reaction Guide gives individual descriptions, examples, and mechanisms of more than 150 of the most common reactions encountered in undergraduate organic chemistry.

Alkanes Alkenes Alkynes Substitution (SN2) Substitution (SN1)
Elimination Reactions Alcohols and Thiols Organometallics Epoxides Dienes
Aromatics (Arenes) Aldehydes and Ketones Carboxylic Acids Esters Acyl 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 HCl Addition of HBr Addition of HI
Addition of H3O(+) Chlorination [Cl2] Bromination [Br2]
Iodination [I2] Chlorohydrin formation [Cl2/H2O] Bromohydrin formation [Br2/H2O]
Iodohydrin formation [I2/H2O] 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]
Rearrangements (H shift) Rearrangements (Alkyl shift)

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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

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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(–)] 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]

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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]

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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

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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 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

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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]

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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

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Reactions of Dienes
Diels–Alder reaction Polymerization 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 ketones Side chain bromination 

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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 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 [H2CrOor 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

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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]

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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 esters Claisen 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 reagents Conjugate addition of other nucleophiles

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Reactions of Amides
Dehydration of amides to nitriles [P2O5] Hofmann rearrangement

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

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Miscellaneous
Robinson annulation Alkylation of enamines Oxidative cleavage of vicinal diols
Reduction of thioacetals to alkanes [Raney Ni]

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