ID Name

1 Formation of acetals and ketals from aldehyde

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