data_source stringclasses 1
value | prompt listlengths 2 2 | ability stringclasses 1
value | reward_model dict | extra_info dict |
|---|---|---|---|---|
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][cH:8][c-:9][cH:10][cH:11]1.[Li+:12].[CH3:14][C:15]([CH3:16])([CH3:17])[OH:18].[CH2:19]=[CH:20][CH2:21][Br:22]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[C:6]1[cH:7]=[CH:8][CH2:9][CH:10]=[CH... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch reduction and tandem alkylation of N,N-dimethylbenzamide with allyl bromide"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[C:1]1([C:17](=[O:18])[Cl:22])([CH2:8][CH:7]([CH2:9]2)[CH2:10]3)[CH2:2][C:3]2([c:11]5[cH:12][cH:13][cH:14][cH:15][cH:16]5)[CH2:4][CH:5]3[CH2:6]1.[O:19]=[S:20]=[O:21].[ClH:23]\"}, {\"step_id\": 2, \"products\": \"[C:1]1([C:17](=[O:18])[O:24][n:25]6[c:26](=[S:27])[cH... | {
"difficulty": "hard",
"family": "Barton Decarboxylation",
"name": "Barton Decarboxylation of 3-phenyladamantane-1-carboxylic acid to 1-chloro-3-phenyladamantane"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:2][C:1]([CH3:3])([CH3:4])[CH:5]1[CH2:6][CH2:7][C:8](=[N:15][NH:16][S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][c:23]([CH3:24])[cH:25][cH:26]2)[CH:10]([CH2:11][CH:12]=[CH2:13])[CH2:14]1.[OH2:9]\"}, {\"step_id\": 2, \"products\": \"[CH3:2][C:1]([CH3:3])([CH3:4]... | {
"difficulty": "hard",
"family": "Shapiro Reaction",
"name": "Shapiro reaction of 2-allyl-4-tert-butylcyclohexanone with D2O quench"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][N:8]=[C:15]2[CH2:14][CH2:13][CH:12]([CH3:11])[CH2:18][CH2:17]2)[cH:9][cH:10]1.[OH2:16]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][NH:8][C:15]2=[CH:14][CH2:13][CH:12]([CH3:11])[CH2:18][C... | {
"difficulty": "hard",
"family": "Fischer Indole Synthesis",
"name": "Synthesis of 6-methoxy-3-methyl-2,3,4,9-tetrahydro-1H-carbazole via Fischer Indole Synthesis"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[O:1]=[C:2]([CH2:3][Br:4])[N:5]([CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[C:14](=[CH2:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[Sn:22]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH2:33][CH3:34].[C:38]([CH3:39])... | {
"difficulty": "hard",
"family": "Radical Cyclization Cascade (Bu3SnH)",
"name": "4-exo-trig radical cyclization of N-benzyl-N-(1-phenylvinyl)-2-bromoacetamide to a beta-lactam"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[s:19]1[cH:20][c:21]([CH3:22])[n+:23]([CH3:24])[c-:25]1.[CH3:26][CH2:27][NH+:28]([CH2:29][CH3:30])[CH2:31][CH3:32].[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:6](=[O:7]))[cH:8][cH:9]1.[O:10]=[C:11]1[CH:12]=[CH:13][C:14]([CH3:15])([CH3:16])[CH2:17][CH2:18]1\"}, {\"step_id\": ... | {
"difficulty": "hard",
"family": "Stetter Reaction (NHC-catalyzed)",
"name": "Stetter reaction of 4-chlorobenzaldehyde and 4,4-dimethylcyclohex-2-enone"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH2:1]=[CH:2]-[CH2:3]-[CH2:4]-[N:5]1-[CH:6]([CH3:7])-[CH2:8]-[CH2:9]-[CH:10]1-[C:11](=[O:12])-[Cl:14].[O:13]=[S:15]=[O:16].[ClH:17]\"}, {\"step_id\": 2, \"products\": \"[CH2:1]=[CH:2]-[CH2:3]-[CH2:4]-[N:5]1-[CH:6]([CH3:7])-[CH2:8]-[CH2:9]-[CH:10]1-[C:11](=[O:12])-... | {
"difficulty": "hard",
"family": "Barton Decarboxylation",
"name": "Barton decarboxylation of 1-(but-3-en-1-yl)-5-methylpyrrolidine-2-carboxylic acid with tandem 5-exo-trig radical cyclization"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][C:2]12[CH2:3][CH2:4][C:5]([CH3:6])([CH2:7]1)[CH2:8][C:9]2=[N:22][NH:21][S:18](=[O:19])(=[O:20])[c:15]3[cH:14][cH:13][c:12]([CH3:11])[cH:17][cH:16]3.[OH2:10].[CH3-:23].[Li+:24].[CH3-:25].[Li+:26].[cH:27]1[cH:28][cH:29][c:30]([CH:33]=[O:34])[cH:31][cH:32]1.[O... | {
"difficulty": "hard",
"family": "Shapiro Reaction",
"name": "Shapiro reaction of 1,4-dimethylbicyclo[2.2.1]heptan-2-one with benzaldehyde"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH2:10]=[C:5]1[C:6](=[CH2:11])[cH:1][n:2][c:3]([CH3:4])[c:7]1[O:8][CH3:9].[CH2:12]=[CH:13][C:14](=[O:15])[O:16][CH3:17]\"}, {\"step_id\": 2, \"products\": \"[CH3:9][O:8][c:7]1[c:6]2[CH2:11][CH:13]([C:14](=[O:15])[O:16][CH3:17])[CH2:12][CH2:10][c:5]2[c:3]([CH3:4])[... | {
"difficulty": "hard",
"family": "Electrocyclic Ring Opening + Diels-Alder Cascade",
"name": "Cascade electrocyclic ring opening of a cyclobutapyridine and intermolecular Diels-Alder cycloaddition"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[cH:9][cH:10]1.[C-:11]#[O+:12].[H:25][H:26].[C-:20]#[O+:21].[Rh:19]([H:27])(P(c1ccccc1)(c2ccccc2)c3ccccc3)(P(c4ccccc4)(c5ccccc5)c6ccccc6)\"}, {\"step_id\": 2, \"products\": \"[Rh:19]([H:27])(P(c1ccccc1)(c2ccccc2)c3... | {
"difficulty": "hard",
"family": "Rhodium-Catalyzed Hydroformylation",
"name": "Hydroformylation of 4-methoxystyrene to 2-(4-methoxyphenyl)propanal"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH2:8]=[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]1=[C:7]([CH3:9])[O:10][CH2:11][CH2:12][CH:13]=[CH2:14]\"}, {\"step_id\": 2, \"products\": \"[CH3:9][C:7]12[c:1]3[c:2]([CH2:8][CH2:14][CH:13]1[CH2:12][CH2:11][O:10]2)[cH:3][cH:4][cH:5][cH:6]3\"}]"
} | {
"difficulty": "hard",
"family": "Electrocyclic Ring Opening + Diels-Alder Cascade",
"name": "Intramolecular Diels-Alder cascade of 1-(but-3-en-1-yloxy)-1-methylbenzocyclobutene"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[Li+:30].[CH3:13][O:12][C:11]1=[C:14]([H:15])[C:16]([C:17](=[O:18])[N:19]([CH3:20])[CH3:21])[C:22]([H:23])=[C:24]([H:25])[C-:26]1([H:27]).[Li:40].[CH3:31][C:32]([CH3:33])([CH3:34])[O:35][H:36].[CH3:41][I:42]\"}, {\"step_id\": 2, \"products\": \"[Li+:30].[CH3:13][O:... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch reduction-alkylation of N,N-dimethyl-3-methoxybenzamide with methyl iodide"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:7]-[C:5](=[O:6])-[CH2:4]-[CH2:3]-[CH:2]=[N+:8]([H:8])-[CH2:9]-[CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)-[CH:17]=[CH2:18].[OH2:1].[CH3:19]-[C:20](=[O:21])-[O-:22]\"}, {\"step_id\": 2, \"products\": \"[CH3:7]-[C:5](=[O:6])-[CH2:4]-[CH2:3]-[CH:2](-[CH2... | {
"difficulty": "hard",
"family": "Aza-Cope / Mannich Cascade (Overman)",
"name": "Overman cascade of 2-phenylbut-3-en-1-amine and levulinaldehyde to form a substituted pyrrolidine"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[C:1]1([O:7][CH3:8])=[C:2][C:3]=[C:4][C:5]=[C:6]1.[Li+:14]\"}, {\"step_id\": 2, \"products\": \"[C:1]1([O:7][CH3:8])=[C:2]([H:18])[C:3]=[C:4][C:5]=[C:6]1.[C:9]([CH3:10])([CH3:11])([CH3:12])[O-:13]\"}, {\"step_id\": 3, \"products\": \"[C-:1]1([O:7][CH3:8])=[C:2]([H:... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch reduction and alkylation of anisole"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:13][CH2:14][CH2:15][CH2:16][Sn:17]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25]).[CH3:30][C:29]([CH3:31])([C:28]#[N:27])[H:26].[CH3:35][C:34]([CH3:36])([C:37]#[N:38])[N:32]=[N:33]\"}, {\"step_id\": 2, \"products\": \"[c:1]1([CH2:7][CH2:8]... | {
"difficulty": "hard",
"family": "Radical Cyclization Cascade (Bu3SnH)",
"name": "Tandem 5-exo-trig/5-exo-trig cyclization of 1-(2-bromoethyl)-2-(3-(allyloxy)-2-methylprop-1-en-1-yl)benzene"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[c:1]1([N:7][N:8]=[C:11]2[C:13][C:14][C:15][C:16][C:17]2)[c:2][c:3][c:4]([O:9][C:10])[c:5][c:6]1.[O:12]\"}, {\"step_id\": 2, \"products\": \"[c:1]1([N:7][N:8][C:11]2=[C:13][C:14][C:15][C:16][C:17]2)[c:2][c:3][c:4]([O:9][C:10])[c:5][c:6]1\"}, {\"step_id\": 3, \"prod... | {
"difficulty": "hard",
"family": "Fischer Indole Synthesis",
"name": "Synthesis of 6-methoxy-2,3,4,9-tetrahydro-1H-carbazole from 4-methoxyphenylhydrazine and cyclohexanone"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[C:8]1[C:2](=[N:9][N:10][S:11](=[O:12])(=[O:13])[c:14]2[c:15][c:16][c:17]([C:20])[c:18][c:19]2)[C:3]2[C:4][C:5][C:6]1[C:7]2.[O:1]\"}, {\"step_id\": 2, \"products\": \"[Li:22][N:9][N:10][S:11](=[O:12])(=[O:13])[c:14]2[c:15][c:16][c:17]([C:20])[c:18][c:19]2.[Li:24][C... | {
"difficulty": "hard",
"family": "Shapiro Reaction",
"name": "Shapiro reaction of norcamphor with acetone electrophile"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[F:1][C:2]([F:3])([F:4])[C:5]1([N:6]=[N:7][C:8]([C:9]([F:10])([F:11])[F:12])=[N:13][N:14]1)[C:18]2[C:19]3[C:20][C:21][C:16]([C:22]3)[C:17]2\"}, {\"step_id\": 2, \"products\": \"[F:1][C:2]([F:3])([F:4])[c:5]1[n:6][c:8]([C:9]([F:10])([F:11])[F:12])[c:18]2[C:19]3[C:20... | {
"difficulty": "hard",
"family": "Inverse-Demand DA + Retro-DA Cascade",
"name": "Inverse-demand DA of 3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine with norbornene followed by N2 extrusion"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][N:8]=[C:15]2[CH2:14][CH2:13][CH:12]([CH3:11])[CH2:18][CH2:17]2)[cH:9][cH:10]1.[OH2:16]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][NH:8][C:15]2=[CH:14][CH2:13][CH:12]([CH3:11])[CH2:18][C... | {
"difficulty": "hard",
"family": "Fischer Indole Synthesis",
"name": "Synthesis of 6-methoxy-3-methyl-2,3,4,9-tetrahydro-1H-carbazole via Fischer Indole Synthesis"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[C:15]1[N:16]([CH3:17])[C:18]([CH3:19])=[CH:20][S:21]1.[CH3:22][CH2:23][NH+:24]([CH2:25][CH3:26])[CH2:27][CH3:28]\"}, {\"step_id\": 2, \"products\": \"[O-:1][CH:2]([C:15]1[N+:16]([CH3:17])[C:18]([CH3:19])=[CH:20][S:21]1)[c:3]2[c:4][c:5][c:6][c:7][c:8]2[O:9][CH:10]=... | {
"difficulty": "hard",
"family": "Stetter Reaction (NHC-catalyzed)",
"name": "Intramolecular Stetter Reaction to form a 2-substituted benzofuran-3-one"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[C:9]([H])([H])=[C:5]1[C:4]([H])=[C:3]([H])[C:2]([H])=[C:1]([H])[C:6]1=[C:7]([O:8][H])[C:10]([H])([H])[C:11]([H])([H])[C:12]([H])=[C:13]([H])[H]\"}, {\"step_id\": 2, \"products\": \"[c:1]1([H])[c:2]([H])[c:3]([H])[c:4]([H])[c:5]2[C:9]([H])([H])[C:12]([H])([C:11]([H... | {
"difficulty": "hard",
"family": "Electrocyclic Ring Opening + Diels-Alder Cascade",
"name": "Tandem Electrocyclic Ring Opening / Intramolecular Diels-Alder of 1-(but-3-en-1-yl)benzocyclobuten-1-ol to form a bridged tricyclic system"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][C:2]([CH3:3])([CH:4]=[CH2:5])[CH2:6][NH+:7]=[CH:11][C:9](=[O:10])[CH3:8].[CH3:13][C:14](=[O:15])[O-:16].[OH2:12]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][C:2]([CH3:3])=[CH:4][CH2:5][CH:11]([C:9](=[O:10])[CH3:8])[NH+:7]=[CH2:6].[CH3:13][C:14](=[O:15])[O-... | {
"difficulty": "hard",
"family": "Aza-Cope / Mannich Cascade (Overman)",
"name": "Overman Aza-Cope/Mannich Cascade of 2,2-dimethylbut-3-en-1-amine and pyruvaldehyde"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[C:2]1(=[N:26][NH:25][S:22](=[O:23])(=[O:24])[c:19]2[cH:18][cH:17][c:16]([CH3:15])[cH:21][cH:20]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3.[OH2:1]\"}, {\"step_id\": 2, \"products\": \"[C:2]1(=[N:26][N-:25][S:22](=[O:23])(... | {
"difficulty": "hard",
"family": "Shapiro Reaction",
"name": "Shapiro reaction of 2-benzylcyclohexanone to 3-benzylcyclohex-1-ene"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[O-:1][C:2](=[O:3])[C.:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH-:11][CH:12]=[CH:13]1.[Na+:14].[Na:15].[C:16]([CH3:17])([CH3:18])([CH3:19])[OH:20].[CH3:21][I:22]\"}, {\"step_id\": 2, \"products\": \"[O-:1][C:2](=[O:3])[C.:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch alkylation of sodium 1-naphthoate with methyl iodide"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:15]-[CH2:16]-[n+:17]1[c:21]([CH3:22])[cH:20][s:19][c:18]1.[CH3:23][CH2:24][NH+:25]([CH2:26][CH3:27])[CH2:28][CH3:29]\"}, {\"step_id\": 2, \"products\": \"[CH3:1]-[c:2]1[cH:3][cH:4][c:5]([CH:6]([O-:7])[c:18]2[s:19][cH:20][c:21]([CH3:22])[n+:17]2[CH2:16][CH3:15]... | {
"difficulty": "hard",
"family": "Stetter Reaction (NHC-catalyzed)",
"name": "Stetter Reaction of 5-methylfurfural and ethyl vinyl ketone catalyzed by 3-ethyl-4-methylthiazol-3-ium"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[Rh:1]([H:2])([C:3](=[O:4]))([P:5]([CH3:6])([CH3:7])[CH3:8])([P:9]([CH3:10])([CH3:11])[CH3:12]).[P:13]([CH3:14])([CH3:15])[CH3:16].[c:17]1[c:18][c:19][c:20][c:21][c:22]1[CH2:23][CH2:24][CH:25]=[CH2:26].[C-:27]#[O+:28].[H:29][H:30]\"}, {\"step_id\": 2, \"products\":... | {
"difficulty": "hard",
"family": "Rhodium-Catalyzed Hydroformylation",
"name": "Hydroformylation of 4-phenyl-1-butene to 5-phenylpentanal"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[c:1]1([C:7](=[O:8])[O-:9])[cH:2][c:3]([O:10][CH3:11])[cH:4][cH:5][cH:6]1.[Li+:12]\"}, {\"step_id\": 2, \"products\": \"[C:1]1([C:7](=[O:8])[O-:9])[CH:2]=[C:3]([O:10][CH3:11])[CH-:4][CH:5]=[CH:6]1.[Li+:12]\"}, {\"step_id\": 3, \"products\": \"[C-:1]1([C:7](=[O:8])[... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch reductive alkylation of 3-methoxybenzoic acid"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][C:2]1=[CH:3][CH-:4][CH:5]=[CH:6][CH:7]1.[Li+:8].[Li:14].[CH3:9][C:10]([CH3:11])([CH3:12])[OH:13].[CH3:15][C:16]([CH3:17])([CH3:18])[OH:19]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][C:2]1=[CH:3][CH2:4][CH:5]=[CH:6][CH:7]1.[Li+:8].[Li:14].[CH3:9][C:10]([CH... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch reduction of toluene"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[c:1]1([NH:7][N:8]=[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[cH:2][cH:3][cH:4][cH:5][cH:6]1.[OH2:9]\"}, {\"step_id\": 2, \"products\": \"[c:1]1([NH:7][NH:8][C:10]2=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[cH:2][cH:3][cH:4][cH:5][cH:6]1.[OH2:9]\"}, {\"step_... | {
"difficulty": "hard",
"family": "Fischer Indole Synthesis",
"name": "Synthesis of 1,2,3,4-tetrahydrocarbazole from phenylhydrazine and cyclohexanone"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH-:7][cH:8][cH:9]1.[Li+:10]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[CH:7]([H:16])[cH:8][cH:9]1.[CH3:11][C:12]([CH3:13])([CH3:14])[O-:15]\"}, {\"step_id\": 3, \"products\": \"[CH3:1][O:2][C-... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch reduction and alkylation of 3-methylanisole"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[c:2]1[c:3][c:4][c:5][c:6][c:7]1[CH2:8][CH:9]=[CH2:10].[Sn:11]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:20][CH2:21][CH2:22][CH3:23].[N:24]#[C:25][CH:26]([CH3:27])[CH3:28].[N:29]#[N:30].[N:33]#[C:32][C:31]([CH3:34])[CH3:35]\"}, {\"step... | {
"difficulty": "hard",
"family": "Radical Cyclization Cascade (Bu3SnH)",
"name": "Radical cyclization of 3-(2-bromophenyl)-1-propene to 1-methylindane"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[n:1]1[cH:2][c:3](=[CH2:8])[c:4](=[CH2:7])[cH:5][c:6]1[O:9][CH3:10].[CH2:11]=[CH:12][C:13](=[O:14])[O:15][CH3:16]\"}, {\"step_id\": 2, \"products\": \"[n:1]1[cH:2][c:3]2[c:4]([cH:5][c:6]1[O:9][CH3:10])[CH2:7][CH2:11][CH:12]([C:13](=[O:14])[O:15][CH3:16])[CH2:8]2\"}... | {
"difficulty": "hard",
"family": "Electrocyclic Ring Opening + Diels-Alder Cascade",
"name": "Cascade reaction of 6-methoxy-1,2-dihydrocyclobuta[c]pyridine with methyl acrylate"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1=[N:20][NH:19][S:16](=[O:17])(=[O:18])[c:13]1[cH:12][cH:11][c:10]([CH3:9])[cH:15][cH:14]1.[OH2:8]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH-:6][C:7]1=[N:20][N-:19][S:16](=[O:17])(=[O:... | {
"difficulty": "hard",
"family": "Shapiro Reaction",
"name": "Shapiro reaction of 2-methylcyclohexanone to 3-methylcyclohexene"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[NH2:20][C:21](=[O:22])[c:2]1[cH:3][cH:4][c-:5][cH:6][cH:7]1.[Li+:8].[CH3:9][C:10]([CH3:11])([CH3:12])[OH:13].[Li:15].[CH2:16]=[CH:17][CH2:18][Br:19]\"}, {\"step_id\": 2, \"products\": \"[NH2:20][C:21](=[O:22])[c:2]1[cH:3]=[cH:4][CH2:5][cH:6]=[cH:7]1.[O-:13][C:10](... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch reduction-alkylation of benzamide with allyl bromide"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][O:2][c:3]1[c:4]([CH2:10])[c:5]([c:6]([CH3:7])[n:8][cH:9]1)=[CH2:11].[CH2:12]=[CH:13][C:14](=[O:15])[O:16][CH3:17]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][O:2][c:3]1[c:4]2[c:5]([c:6]([CH3:7])[n:8][cH:9]1)[CH2:10][CH:13]([C:14](=[O:15])[O:16][CH3:17])[CH... | {
"difficulty": "hard",
"family": "Electrocyclic Ring Opening + Diels-Alder Cascade",
"name": "Cascade of 5-methoxy-2-methyl-1,2-dihydrocyclobuta[c]pyridine with methyl acrylate"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][c:2]1[cH:3][cH:4][c:5]([o:6]1)[CH:7]=[O:8].[CH3:9][CH2:10][C:11](=[O:12])[CH:13]=[CH2:14].[CH3:15][n:16]1[n:17][cH:18][n+:19]([CH3:20])[c-:21]1.[N:22]12[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1=[NH+:29][CH2:30][CH2:31][CH2:32]2\"}, {\"step_id\": 2, \"... | {
"difficulty": "hard",
"family": "Stetter Reaction (NHC-catalyzed)",
"name": "Stetter reaction of 5-methylfurfural and ethyl vinyl ketone"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[C:14][c:13]1[c:12][c:11][c:10]([S:17](=[O:18])(=[O:19])[NH:20][N:21]=[C:1]2[C:3]([C:4])([C:5])[C:6][C:7][C:8][C:9]2)[c:16][c:15]1.[OH2:2]\"}, {\"step_id\": 2, \"products\": \"[C:14][c:13]1[c:12][c:11][c:10]([S:17](=[O:18])(=[O:19])[N-:20][N:21]=[C:1]2[C:3]([C:4])(... | {
"difficulty": "hard",
"family": "Shapiro Reaction",
"name": "Shapiro reaction of 2,2-dimethylcyclohexanone with benzaldehyde to form an allylic alcohol"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[C:1]1([n:2][c:3][n:4][c:5]([C:14])[n:6]1).[C:7]([O:9][C:10][C:11])=[C:8].[C:16]([O:18][C:19][C:20])=[C:17]\"}, {\"step_id\": 2, \"products\": \"[C:1]2([N:6][C:5]([C:14])=[N:4][C:3]=[N:2]2)[C:7]([O:9][C:10][C:11])[C:8].[C:16]([O:18][C:19][C:20])=[C:17]\"}, {\"step_... | {
"difficulty": "hard",
"family": "Inverse-Demand DA + Retro-DA Cascade",
"name": "Sequential Inverse-Demand Diels-Alder Cascade of 2-Methyl-1,3,5-triazine with Ethyl Vinyl Ether to form 4-Methylpyridine"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:28][n+:29]1[c-:30][s:31][cH:32][c:34]1[CH3:33].[CH3:35][CH2:36][NH+:37]([CH2:38][CH3:39])[CH2:40][CH3:41]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][O:2][c:3]1[c:4][c:5][c:6]([CH:7]([O-:8])[c:30]2[n+:29]([CH3:28])[c:34]([CH3:33])[cH:32][s:31]2)[c:9][c:10]1\"... | {
"difficulty": "hard",
"family": "Stetter Reaction (NHC-catalyzed)",
"name": "Stetter reaction of 4-methoxybenzaldehyde and (E)-1-(4-chlorophenyl)-3-phenylprop-2-en-1-one"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][cH:10]1.[O:11]=[C:12]1[CH:13]=[CH:14][CH2:15][CH2:16]1.[CH3:17][CH2:18][N+:19]1=[C-:20][S:21][C:22]([CH3:23])=[C:24]1[CH3:25].[CH3:26][CH2:27][NH+:28]([CH2:29][CH3:30])[CH2:31][CH3:32]\"}, {\"step_id\": 2, \"p... | {
"difficulty": "hard",
"family": "Stetter Reaction (NHC-catalyzed)",
"name": "Intermolecular Stetter reaction of 4-methoxybenzaldehyde and cyclopent-2-en-1-one catalyzed by a thiazolium-derived NHC"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][CH2:2][O:3][C:4]1=[C:5]([H:15])[C:6]([CH3:7])=[C:8]([H:16])[C-:9]([H:17])[C:10]1([H:18]).[Li+:11].[CH3:12][C:13]([CH3:14])([CH3:19])[O:20][H:21].[CH2:22]=[CH:23][CH2:24][Br:25]\"}, {\"step_id\": 2, \"products\": \"[CH3:1][CH2:2][O:3][C:4]1=[C:5]([H:15])[C:6... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch reductive alkylation of 1-ethoxy-3-methylbenzene with allyl bromide"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[O:8]=[C:7]=[C:4]2[c:3][c:2][c:1][c:6][c:5]2[CH2:9]\"}, {\"step_id\": 2, \"products\": \"[c:1]1[c:2][c:3][c:4]2[c:5]([c:6]1)[CH2:9][CH:12]3[CH:13]([C:7]2=[O:8])[C:14](=[O:15])[N:16]([CH3:17])[C:11]3=[O:10]\"}]"
} | {
"difficulty": "hard",
"family": "Electrocyclic Ring Opening + Diels-Alder Cascade",
"name": "Cascade reaction of benzocyclobutenone and N-methylmaleimide"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:9]=[O:10])[cH:7][cH:8]1.[CH2:11]=[CH:12][C:13](=[O:14])[O:15][CH2:16][CH3:17].[CH:18]1=[C:19]([CH3:20])[N:21]([CH2:22][CH3:23])[C:24][S:25]1.[CH3:26][CH2:27][NH+:28]([CH2:29][CH3:30])[CH2:31][CH3:32]\"}, {\"step_id\": 2, \"pr... | {
"difficulty": "hard",
"family": "Stetter Reaction (NHC-catalyzed)",
"name": "Intermolecular Stetter reaction of 4-methoxybenzaldehyde and ethyl acrylate"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[c:1]1[c:2][c:3][c:4][c:5][c:6]1[C:7][C:8](=[O:9])[O:10][C:18](=[N:17][C:11]2[C:12][C:13][C:14][C:15][C:16]2)[NH:19][C:20]3[C:21][C:22][C:23][C:24][C:25]3.[OH:26][N:27]4[C:28]=[C:29][C:30]=[C:31][C:32]4=[S:33].[C:34]=[C:35][C:36][Sn:37]([C:38][C:39][C:40][C:41])([C... | {
"difficulty": "hard",
"family": "Barton Decarboxylation",
"name": "Barton Decarboxylation of phenylacetic acid with allylstannane trap"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[c-:1]1([C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[cH:2][cH:3][cH:4][cH:5][cH:6]1.[Li+:12].[C:13]([CH3:14])([CH3:15])([CH3:16])[O:17][H:18].[Li:19].[C:20]([H:21])([H:22])([H:23])[I:24]\"}, {\"step_id\": 2, \"products\": \"[C:1]1([C:7](=[O:8])[N:9]([CH3:10])[CH3:11])[CH:... | {
"difficulty": "hard",
"family": "Birch Reduction + Alkylation",
"name": "Birch reductive alkylation of N,N-dimethylbenzamide with methyl iodide"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[RhH:12]([C-:13]#[O+:14])([PH3:15])([PH3:16]).[PH3:17].[c:1]1[c:2][c:3][c:4]([OH:18])[c:5]([C:7]=[C:8])[c:6]1.[C-:10]#[O+:11].[H:19][H:20]\"}, {\"step_id\": 2, \"products\": \"[c:1]1[c:2][c:3][c:4]([OH:18])[c:5]([C:7]2[C:8][RhH:12]2([C-:13]#[O+:14])([PH3:15])[PH3:1... | {
"difficulty": "hard",
"family": "Rhodium-Catalyzed Hydroformylation",
"name": "Tandem Hydroformylation-Acetalization of 2-Vinylphenol"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[c:1]1[c:2][c:3][c:4][c:5][c:6]1[CH2:7][NH+:8]([CH2:9][CH:10]=[CH2:11])=[CH:13][CH2:14][CH2:15][C:16](=[O:17])[CH3:18].[OH2:12].[F:19][C:22]([F:20])([F:21])[C:23](=[O:24])[O-:25]\"}, {\"step_id\": 2, \"products\": \"[c:1]1[c:2][c:3][c:4][c:5][c:6]1[CH2:7][NH:8]=[CH... | {
"difficulty": "hard",
"family": "Aza-Cope / Mannich Cascade (Overman)",
"name": "Cascade of N-benzyl allylamine and 4-oxopentanal to form a functionalized cyclopentanone"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[CH3:9][CH:8]=[C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][c:1]1=[CH:7][O:10][CH2:11][CH:12]=[CH2:13]\"}, {\"step_id\": 2, \"products\": \"[CH3:9][CH:8]1[c:6]2[c:5]([H])[c:4]([H])[c:3]([H])[c:2]([H])[c:1]2[CH:7]3[O:10][CH2:11][CH:12]1[CH2:13]3\"}]"
} | {
"difficulty": "hard",
"family": "Electrocyclic Ring Opening + Diels-Alder Cascade",
"name": "Intramolecular Diels-Alder cascade of 7-(allyloxy)-8-methylbicyclo[4.2.0]octa-1,3,5-triene"
} |
named_reaction_synthetic_hard_verified | [
{
"content": "Role: You are an expert Computational Chemist and Mechanism Designer. You prioritize chemical validity and strict SMILES syntax.\n\nTask: Given the starting reactants (SMILES with atom mapping), predict the complete multi-step reaction mechanism.\n\n## Instructions\n\n1. **Reasoning Section (Manda... | mechanism_prediction | {
"ground_truth": "[{\"step_id\": 1, \"products\": \"[O:1]=[C:2]=[C:11]1[CH:10]=[CH:9][CH:8]=[C:5]([O:6][CH3:7])[C:4]1=[CH2:3].[O:12]=[C:13]1[CH:14]=[CH:15][C:16](=[O:17])[N:18]1[CH3:19]\"}, {\"step_id\": 2, \"products\": \"[CH3:19][N:18]1[C:13](=[O:12])[CH:14]2[CH:15]([C:16]1=[O:17])[CH2:3][c:4]3[c:5]([O:6][CH3:7])[... | {
"difficulty": "hard",
"family": "Electrocyclic Ring Opening + Diels-Alder Cascade",
"name": "Thermal cascade of 4-methoxybenzocyclobuten-1-one and N-methylmaleimide"
} |
End of preview. Expand in Data Studio
flower-named-reactions-hard
Gemini-generated hard named-reaction mechanisms in verl RL format, companion to
johnny-w/flower. data_source tag:
named_reaction_synthetic_hard_verified.
- 326 train + 36 validation mechanisms across 10 difficult named-reaction families.
- Generated, atom-mapped, then verified with an RDKit toolkit pass (the
current_verified_toolkit_flashpipeline).
⚠️ Negative result — not used in the final models
This subset is archived for completeness. It was mixed into RL training in the abandoned
v9 / v10 / v11 experiments and degraded Fukuyama performance (e.g. GSPO v11, which
included 652 hard samples, scored only ~2.4% exact pass@1 vs. the 8.3% SOTA). Like the
synthetic pericyclic data, it shifts the model away from the real-chemistry Fukuyama
distribution. The published / SOTA pipeline (qwen3-30b-gspo-v6-ep3, v14-ep3) contains
no synthetic named-reaction data.
Use it only to reproduce the synthetic-data-mismatch finding, not to improve a model.
Families
Fischer Indole Synthesis (44), Shapiro Reaction (42), Electrocyclic Ring Opening + Diels-Alder Cascade (43), Stetter Reaction NHC-catalyzed (41), Inverse-Demand DA + Retro-DA Cascade (34), Birch Reduction + Alkylation (32), Barton Decarboxylation (31), Radical Cyclization Cascade Bu3SnH (29), Rhodium-Catalyzed Hydroformylation (20), Aza-Cope / Mannich Cascade Overman (10).
Schema (verl RL format)
data_source:named_reaction_synthetic_hard_verifiedprompt: list of chat messages in verl prompt formatability: task tagreward_model.ground_truth: ground-truth mechanism trajectory (FlowER-style atom-mapped SMILES)extra_info:{difficulty, family, name}
Load
from datasets import load_dataset
ds = load_dataset("johnny-w/flower-named-reactions-hard")
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