Reactions
Free radical chlorination [hν, Cl2]
Free radical bromination [hν, Br2]
Chlorohydrin formation [Cl2/H2O]
Bromohydrin formation [Br2/H2O]
Deprotonation (acetylide formation)
Addition of HCl, HBr, or HI (once)
Addition of HCl, HBr, or HI (twice)
Alkyne formation via elimination
Ammonium salt formation [RNH2]
Alkyl chloride formation [HCl]
SN1 w/ rearrangement [alkyl shift]
SN1 w/rearrangement [hydride shift]
Alcohol formation [ether cleavage]
E2: Alkenes from alkyl halides
E1: Alkenes from alkyl halides
Alkyne formation via elimination
Alkenes from alcohols [strong acid]
E1 with rearrangement [hydride shift]
Grignard formation [alkyl halides]
Addition of Grignards to aldehydes
Reaction of Grignards with CO2
Addition of Gilman to acyl halides
Grignard formation [alkenyl halides]
Addition of Grignards to ketones
Reaction of Grignards with acid [H+]
Addition of Grignards to esters
Formation of organolithium reagents
Addition of Gilman reagents to enones
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
Protonation [onium ion formation]
Conversion to alkyl chlorides [SOCl2]
Oxidation to ketones [PCC + others]
Conversion to alkyl bromides [PBr3]
Oxidation to carboxylic acids [H2CrO4 + others]
Aryne Formation (SNAr via arynes)
Chlorination [Cl2 plus catalyst]
Friedel Crafts alkylation [R-X plus catalyst]
Bromination [Br2 plus catalyst]
Friedel Crafts acylation [RCOX plus catalyst]
Nucleophilic Aromatic Substitution (SNAr)
Reduction of aldehydes [LiAlH4]
Grignard addition to aldehydes
Wolff-Kishner: reduction to alkanes
Clemmensen reduction to alkanes
Wittig reaction: alkene formation
Oxidation to carboxylic acids [Tollens]
Reduction of aldehydes [NaBH4]
Oxidation to carboxylic acid [H2CrO4 or KMnO4]
Deprotonation [carboxylate formation]
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]
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]
Amide Formation from Acid Halides
Hydrolysis to carboxylic acids
Reduction of thioacetals to alkanes [Raney Ni]
Hell-Vollhard-Zolinsky Reaction
Malonic Ester / Acetoacetic Ester Synthesis