ID Name SMIRKS FunctionalGroup TransformType 1 Formation of acetals and ketals from aldehydes/ketones [C:7][O:6][C:1][O:3][C:4]>>[C:7][O:6][H].[C:4][O:3][H].[O]=[C:1] ACETALS and KETALS FGE 2 Synthesis of acid chlorides From Carboxylic Acids [C:3][C:1](=[O:2])[Cl]>>[C:3][C:1](=[O:2])[O][H] ACID CHLORIDES FGE 3 Synthesis of alcohols from acid chlorides [#6:7][C:1](=[O:2])[Cl]>>[#6:7][C:1]([H])([H])[O:2][H] ALCOHOLS FGE 4 Synthesis of alcohols from anhydrides [#6:7][C:1](=[O:2])[O][C](=[O])[C]>>[#6:7][C:1]([H])([H])[O:2][H] ALCOHOLS FGE 5 Reduction of esters to alcohols [#6:7][C:1](=[O:2])[O:3][#6:4]>>[#6:7][C:1]([H])([H])[O:2][H].[O:3]([H])[#6:4] ALCOHOLS FGE 6 Hydration of alkenes [H][C:2][C:1][O][H]>>[C:1]=[C:2] ALCOHOLS FGE 7 Ether formation from alcohols [C:1][O:2][C:3]>>[C:1][O:2][H].[H][O][C:3] ETHERS FGE 8 Reduction of aldehydes/ketones "[H,C:4][C:1]([H])([#6:5])[O:2][H]>>[H,C:4][C:1](=[O:2])[#6:5]" ALCOHOLS FGE 9 Reduction of conjugated aldehydes/ketones "[H,C:4][C:1]([H])([O:2][H])[C:5][C:3]>>[H,C:4][C:1](=[O:2])[C:5][C:3]" ALCOHOLS FGE 10 Halohydrin formation from Alkenes [C:1]([O][H])[C:2][Cl]>>[C:1]=[C:2] ALCOHOLS-FUNCTIONALIZED FGE 11 Aldehydes From Acetals [C:7][O:6][C:1][O:3][C:4]>>[C:7][O:6][H].[C:4][O:3][H].[O]=[C:1] ALDEHYDES or KETONES FGE 12 Oxidation of secondary alcohols to ketones [C:3][C:1]([C:4])=[O:2]>>[C:3][C:1]([H])([C:4])[O:2][H] ALDEHYDES or KETONES FGE 13 Ozonolysis of alkenes [C:1]=[C:2]>>[C:1]=[O].[C:2]=[O] ALDEHYDES or KETONES FGE 14 Hydration of terminal alkynes [C:1]([H])([H])[C:2]([H])=[O]>>[C:1]#[C:2]([H]) ALDEHYDES FGE 15 Oxidation of vicinal diols to aldehydes or ketones "[O:3]([H])[C:1]([H,C:4])[C:2]([H,C:6])[O:5][H]>>[O:3]=[C:1]([H,C:4]).[C:2]([H,C:6])=[O:5]" ALDEHYDES or KETONES FGE 16 Reduction of nitriles to aldehydes [C:1][C:2](=[O])[H]>>[C:1][C:2]#[N] ALDEHYDES or KETONES FGE 17 Reduction of Alkenes to Alkanes [C:1]([H])[C:2]([H])>>[C:1]=[C:2] ALKANES FGE 18 Reduction of cyclic alkenes [C:1]([H])1[C:2]([H])[C:3]([H])[C:4]([H])[C:5]([H])[C:6]([H])1>>[C:1]1[C:2]=[C:3][C:4]=[C:5][C:6]=1 ALKANES FGE 19 Reduction of alkyl halides [C:1]([H])[C:2]>>[Cl][C:1][C:2] ALKANES FGE 20 Reduction of Ketones or Aldehydes [C:3][C:1]([H])([H])[C:2]>>[C:3][C:1](=[O])[C:2] ALKANES FGE 21 Reduction of Alkynes to Alkenes [C:1]([H])=[C:2]([H])>>[C:1]#[C:2] ALKENES FGE 22 Beta HX elimination [C:3][C:2]=[C:1]>>[C:3][C:1][C:2]([H])[Cl] ALKENES FGE 23 Alkene formation from Sulfonate Esters (elimination) [C:1]=[C:2]>>[C:1]([H])[C:2][O][S](=[O])(=[O])([C]([H])([H])([H])) ALKENES FGE 24 Alkene formation from Ammonium Salts (elimination) [C:3][C:1]([C:2]([H]))[N]([C])([C])>>[C:3][C:1]=[C:2] ALKENES FGE 25 Alkyne formation from Alkenyl Halides (elimination) [C:1]#[C:2]>>[Br][C:2]=[C:1][H] ALKYNES FGE 26 Synthesis of amides from carboxylic acids [N][C:1](=[O:2])[C:7]>>[C:7][C:1](=[O:2])[O][H] AMIDES FGE 27 Synthesis of amides from acyl chloride [#6:4][N:5][C:1]=[O:2]>>[#6:4][N:5][H].[O:2]=[C:1][Cl] AMIDES FGE 28 Synthesis of amides from esters [N:3][C:1](=[O:2])[C:7]>>[C:7][C:1](=[O:2])[O][C]([H])([H])[C]([H])([H])([H]).[N:3][H] AMIDES FGE 29 Synthesis of amides from anhydrides [N:3][C:1](=[O:2])[C:7]>>[C:7][C:1](=[O:2])[O][C](=[O])[C]([H])([H])[C]([H])([H])([H]).[N:3][H] AMIDES FGE 30 Catalytic hydration of nitriles to amides [C:1][C:2](=[O])[O][H]>>[C:1][C:2]#[N] AMIDES FGE 31 Reduction of alkyl azides to amines [C:2][N:1]([H])([H])>>[N-]=[N+]=[N:1][C:2] AMINES FGE 32 Amines From Imides [C:2][N:1]([H])([H])>>[C:2][N:1]([C](=O)[C]([H])([H])[C]([H])([H])([H]))([C](=O)[C]([H])([H])[C]([H])([H])([H])) AMINES FGE 33 Amines From Halides [C:2][NX3:1]>>[NX3:1][H].[C:2][Cl] AMINES FGE 34 Reduction of nitriles to amines [C:1][C:2]([H])([H])[N:3]([H])[H]>>[N:3]#[C:2][C:1] AMINES FGE 35 Reduction of nitro compounds to amines or anilines [#6:1][N:2]([H])([H])>>[#6:1][NX3+:2](=[O])[O-] AMINES FGE 36 Synthesis of anhydrides [O:6]=[C:5][O:3][C:1]=[O:2]>>[O:2]=[C:1][O:3][H].[O:6]=[C:5][Br] ANHYDRIDES FGE 37 Carboxylic acids From Acid chlorides [C:3][C:1](=[O:2])[O][H]>>[C:3][C:1](=[O:2])[Cl] CARBOXYLIC ACIDS FGE 38 Carboxylic acids From Anhydrides [C:3][C:1](=[O:2])[O][H]>>[C:3][C:1](=[O:2])[O][C](=[O])[C]([H])([H])[C]([H])([H])([H]) CARBOXYLIC ACIDS FGE 39 Carboxylic acids From Esters [C:3][C:1](=[O:2])[O][H]>>[C:3][C:1](=[O:2])[O][C]([H])([H])[C]([H])([H])([H]) CARBOXYLIC ACIDS FGE 40 Carboxylic acids From Amides [C:3][C:1](=[O:2])[O][H]>>[C:3][C:1](=[O:2])[N]([H])([H]) CARBOXYLIC ACIDS FGE 41 Oxidation of primary alcohols to carboxylic acids [O:2]=[C:1][O][H]>>[C:1]([H])([H])[O:2][H] CARBOXYLIC ACIDS FGE 42 Decarboxylation [C:5]([H])[C:1](=[O:2])[O:3][H]>>[H][O:3][C:1](=[O:2])[C:5][C](=[O])[O][H] CARBOXYLIC ACIDS FGE 43 Hydrolysis of nitriles to carboxylic acids [C:1][C:2](=[O])[O][H]>>[C:1][C:2]#[N] CARBOXYLIC ACIDS FGE 44 Birch reduction [C:1]([H])1[C:2]=[C:3][C:4]([H])[C:5]=[C:6]1>>[C:1]1=[C:2][C:3]=[C:4][C:5]=[C:6]1 DIENES FGE 45 Hydroxylation of alkenes [H][O][C:1][C:2][O][H]>>[C:1]=[C:2] DIOLS FGE 46 Cleavage of epoxides [O][C:1][C:2][O]>>[C:1]1O[C:2]1 DIOLS FGE 47 Enamine formation [N:1][C:2]=[C:3]>>[N:1][H].[O]=[C:2][C:3][H] ENAMINES FGE 48 Oxidation of alkenes with peracids [C:2]([H])1[C:1][O:3]1>>[C:1]=[C:2][C]([H])([H])([H]).[C]([H])([H])([H])[C](=[O])[O][O:3][H] EPOXIDES FGE 49 Epoxide formation from Halohydrins [C:2]1[C:1][O:3]1>>[C:1]([O:3][H])[C:2][Cl] EPOXIDES FGE 50 Fischer esterification [O:2]=[C:1][O:6][C:8]>>[H][O:6][C:8].[O:2]=[C:1][O][H] ESTERS FGE 51 Acylation with acid chlorides [O:2]=[C:1][O:6][C:8]>>[H][O:6][C:8].[O:2]=[C:1][Cl] ESTERS FGE 52 Acylation with anhydrides [O:2]=[C:1][O:6][C:8]>>[H][O:6][C:8].[O:2]=[C:1][O][C](=[O])[C]([H])([H])([H]) ESTERS FGE 53 Esterification of alcohols [O:2]=[C:1][O:6][#6:8]>>[H][O:6][#6:8].[O:2]=[C:1][O][C]([H])([H])([H]) ESTERS FGE 54 Oxidation of ketones I [C:1][C:2](=[O])[O][C:3]>>[C:1][C:2](=[O])[C:3] ESTERS FGE 55 Oxidation of ketones II [C:3][C:2](=[O])[O][C:1]>>[C:1][C:2](=[O])[C:3] ESTERS FGE 56 Williamson ether synthesis [C:1][O:2][C:4]>>[C:1][O:2][H].[C:4][Cl] ETHERS FGE 57 Halogenation of alcohols with hydrogen halides [C:1][Cl:2]>>[C:1][O][H].[Cl:2][H] HALIDES (ALKYL) FGE 58 Halogenation [#6:1][Cl]>>[#6:1]([H]) HALIDES (ALKYL) FGE 59 Hydrogen halide addition to alkenes [Cl][C:1][C:3]([H])>>[C:1]=[C:3] HALIDES (ALKYL) FGE 60 Halogen addition to alkenes [Cl][C:1][C:3]([Cl])>>[C:1]=[C:3] HALIDES (ALKYL) FGE 61 Hydrogen halide addition to alkynes [Cl:3][C:2]=[C:1][H:4]>>[C:1]#[C:2].[Cl:3][H:4] HALIDES (ALKENYL) FGE 62 Condensation of primary amines and oxocompounds [C:2]=[N][H]>>[O]=[C:2] IMINES FGE 63 Hydartion of alkynes [C:1]([H])([H])[C:2](=[O])[C:3]([H])([H])>>[C:1]([H])([H])[C:2]#[C:3] KETONES or ALDEHYDES FGE 64 Oxidation of vicinal diols [O:3]([H])[C:1]([C:4])[C:2]([C:7])([C:6])[O:5][H]>>[O:3]=[C:1]([C:4]).[C:2]([C:7])([C:6])=[O:5] KETONES or ALDEHYDES FGE 65 Decarboxylation of ?-ketoacid [C:1]([H])[C:2](=[O:3])>>[C:1]([C](=[O])[O][H])[C:2](=[O:3]) KETONES or ALDEHYDES FGE 66 Dehydration of amides to nitriles [C:1][C:2]#[N:3]>>[C:1][C:2](=[O])[N:3]([H])[H] NITRILES FGE 67 Nitration of Aromatic Hydrocarbons [c;H0:1][N+]([O-])=[O]>>[c:1][H] NITRO COMPOUNDS FGE 68 Alkyl Lithium formation from alkyl halides [C:1][Li]>>[C:1][Cl] ORGANOMETALLICS FGE 69 Aryl Halides to Phenols [c:1][O][H]>>[c:1][Cl] PHENOLS FGE 70 Primary Anilines to Phenols [c:1][O][H]>>[c:1][N]([H])([H]) PHENOLS FGE 71 Sulfonation of aromatic hydrocarbons [c:1][S](=[O])(=[O])[O][H]>>[c:1]([H]) SULFONIC ACIDS FGE 72 Grignard Alcohol From Acid Chloride and Organometallics [C:1][C:4]([C:2])([C:6])[O:5][H]>>[C:1][Mg][Br].[C:2][Mg][Br].[C:6][C:4](=[O:5])[Cl] ALCOHOLS C-C 73 Grignard Alcohol From Anhydride and Organometallics [C:1][C:4]([C:2])([C:6])[O:5][H]>>[C:1][Mg][Br].[C:2][Mg][Br].[C:6][C:4](=[O:5])[O][C](=[O])[C]([H])([H])[C]([H])([H])([H]) ALCOHOLS C-C 74 Grignard Alcohol From Esters and Organometallics [C:1][C:4]([C:2])([C:6])[O:5][H]>>[C:1][Mg][Br].[C:2][Mg][Br].[C:6][C:4](=[O:5])[O][C]([H])([H])[C]([H])([H])([H]) ALCOHOLS C-C 75 Grignard Alcohol From Epoxides [C:4][C:2]([H])[C:1][O:3][H]>>[C:2]([H])1[C:1][O:3]1.[C:4][Mg][Br] ALCOHOLS C-C 76 Grignard reaction to carbonyl compounds [C:3][C:1][O:2][H]>>[C:1]=[O:2].[Cl][Mg][C:3] ALCOHOLS C-C 77 ?-hydroxyester formation "[O:6]([H])[C:5]([C:4])([H,C:7])[C:2][C:1](=[O:3])[O:8][C:9]>>[C:4][C:5]([H,C:7])=[O:6].[C:2]([H])[C:1](=[O:3])[O:8][C:9]" ALCOHOLS-ESTERS C-C 78 Alkylation of aldehydes/ketones [C:1][C:2][C:3](=[O:5])[C:4]>>[C:1][I].[C:2]([H])[C:3](=[O:5])[C:4] ALDEHYDES and KETONES C-C 79 Aromatic aldehydes fom Organometallics [c:1][C](=[O])[H]>>[c:1][Mg][Br] ALDEHYDES and KETONES C-C 80 Claisen rearrangement [C:1](=[O:2])[C:6][C:5][C:4]=[C:3]>>[C:6]=[C:1][O:2][C:3][C:4]=[C:5] ALDEHYDE-ALKENES C-C 81 [2+2]-photocycloaddition [C:1]1[C:2][C:3][C:4]1[C:5]>>[C:1]=[C:2].[C:3]=[C:4][C:5] ALKANES C-C 82 [2+2]-photocycloaddition [C:1]1[C:2][C:4]([C;R0:5])[C:3]1>>[C:1]=[C:2].[C:3]=[C:4][C:5] ALKANES C-C 83 Negishi coupling [C:1][C:2]>>[C:1][Zn][Cl].[C:2][Cl] ALKANES C-C 84 Heck reaction [C:1]=[C:2][#6:3]>>[C:1]=[C:2]([H]).[#6:3][Cl] ALKENES C-C 85 Diels-Alder cycloaddition [C:1]1[C:2]=[C:3][C:4][C:5][C:6]1>>[C:1]=[C:2][C:3]=[C:4].[C:5]=[C:6] ALKENES C-C 86 Ring Closing Metathesis [C:1]=[C:2]CCCC[C:3]=[C:4]>>[C:2]1=[C:3]C([H])([H])C([H])([H])C([H])([H])C([H])([H])1.[C:1]=[C:4] ALKENES C-C 87 Wittig reaction [C:1]=[C:2]>>[C:1]=[O].[C:2]([H])[Cl] ALKENES C-C 88 Sonogashira coupling [C:1]=[#6:2][C:3]#[#6:4]([H])>>[C:1]=[#6:2][Cl].[#6:4]([H])#[C:3]([H]) ALKYNES C-C 89 Alkyne-alcohol formation [C:1]#[C:2][C:4]([C:3])([O:6][H])[C:5]>>[C:1]#[C:2][Na].[C:3][C:4](=[O:6])[C:5] ALKYNE-ALCOHOLS C-C 90 Friedel-Crafts alkylation [c:1][C:3]>>[c:1].[Cl][C:3] ARENES C-C 91 Suzuki coupling [c;H0:1][c;H0:2]>>[c;H1:1][Cl].[c;H1:2][B]([O][H])[O][H] BIARYLS C-C 92 Grignard addition to Carbon Dioxide [C:1][C:2](=[O])[O][H]>>[C:1][Mg][Br].[O]=[C:2]=[O] CARBOXYLIC ACIDS C-C 93 "1,5-sigmatropic hydrogen shifts" [C:1]1[C:2]=[C:3][C:4]([H])[C:5]=1>>[C:1]1=[C:2][C:3]=[C:4][C:5]([H])1 DIENES C-C 94 Cope rearrangement [C:1]=[C:2][C:3][C:4][C:5]=[C:6]>>[C:3]=[C:2][C:1][C:6][C:5]=[C:4] DIENES C-C 95 Diketone formation from Ketones and Esters [C:6][O:5][C:1](=[O:2])[C:3][C:7]=[O:8]>>[C]([H])([H])([H])[C:7]=[O:8].[C:3]([H])[C:1](=[O:2])[O:5][C:6] DIKETONES C-C 96 Michael addition [C:1][C:2](=[O:4])[C:3][C:9][C:8]([H])[C:6](=[O:7])[C:5]>>[C:1][C:2](=[O:4])[C:3]([H]).[C:9]=[C:8][C:6](=[O:7])[C:5] DIKETONES C-C 97 Alpha-alkylation of esters [C:1][C:2]([C:7])[C:3](=[O:4])[O:5][C:6]>>[C:1][C:2]([H])[C:3](=[O:4])[O:5][C:6].[C:7][Cl] ESTERS C-C 98 Claisen condensation [C:1][O:5][C:3](=[O:4])[C:2][C:7](=[O:8])[C:6]>>[C:6][C:7](=[O:8])[O][C]([H])([H])([H]).[C:2]([H])[C:3](=[O:4])[O:5][C:1] ESTERS C-C 99 Dieckmann condensation [C:10][O:9][C:7](=[O:8])[C:1]1[C:2][C:3][C:4][C:5](=[O:6])1>>[C:10][O:9][C:7](=[O:8])[C:1]([H])[C:2][C:3][C:4][C:5](=[O:6])[O][C]([H])([H])([H]) ESTERS C-C 100 Ketone formation from acid chlorides and organocuprates [C:1][C:2](=[O:3])[C:4]>>[C:4][Cu-]([C]([H])([H])([H]))[Li+].[C:1][C:2](=[O:3])[Cl] KETONES C-C 101 Friedel-Crafts acylation "[c:1][C,S:2]([H])=[O]>>[c:1][H].[Cl][C,S:2]([H])=[O]" KETONES C-C 102 Ketones formation from Conjugated Ketones with Organometallics [C:1][C:2](=[O:3])[C:6]([H])[C:4][C:5]>>[C:5][C:4][Cu-]([C]([H])([H])[C]([H])([H])([H]))[Li+].[C:1][C:2](=[O:3])[C:6]=[C]([H])([H]) KETONES C-C 103 Robinson annulation [C:1]1[C:2]([C:3])=[C:4][C:5](=[O:6])[C:7]([H])[C:8]1>>[C:1]([H])[C:2](=O)[C:3].[C:4]([H])([H])[C:5](=[O:6])[C:7]=[C:8] KETONES C-C 104 Ketone formation from Nitriles and Organometallics [C:1][C:2](=[O])[C:4]>>[C:1][C:2]#[N].[C:4][Mg][Br] KETONES C-C 105 Aldol reaction [#6:1](=[O:2])[#6:3][#6:5]([#6:9])[O:6][H]>>[#6:1](=[O:2])[#6:3]([H]).[#6:5](=[O:6])[#6:9] KETONE-ALCOHOLS C-C 106 Nitrile formation from Alkyl Halides [C:1][C:2][C:4]#[N:5]>>[C:1][C:2][Br].[N:5]#[C:4][Na] NITRILES C-C 107 Nitrile-alcohol formation from Ketones or Alcohols [N:4]#[C:3][C:1][O:2][H]>>[C:1]=[O:2].[N:4]#[C:3][Na] NITRILE-ALCOHOLS C-C