0f120886-a324-4ae7-b017-63c95bbb0f7b
Predict the mechanism for 10 organic reactions drawn from the FlowER benchmark. Submit final product SMILES, mechanistic steps with electron push notations, and a methodology description. Concerted mechanisms (SN2, pericyclic, N-oxidation) have 1 step. Multi-step reactions (e.g., epoxide opening, Arbuzov) have 2+ steps. See reactions.json and example/worked_example.json in your workspace.
{
"steps": [
[
{
"electron_pushes": [
"pi:diene_1>sigma",
"pi:diene_2>sigma",
"sigma:dienophile>pi"
],
"resulting_state": [
"N#CCCC1C=CC=C1"
]
}
],
[
{
"electron_pushes": [
"lp:N>O"
],
"resulting_state": [
"[O-][n+]1cccc2ccccc21",
"CC(=O)O"
]
}
],
[
{
"electron_pushes": [
"pi:diene_1>sigma",
"pi:diene_2>sigma",
"pi:dienophile>pi"
],
"resulting_state": [
"CC1=CCOC(C(C)c2ccccc2)C1"
]
}
],
[
{
"electron_pushes": [
"lp:N>C",
"sigma:C-Cl>Cl"
],
"resulting_state": [
"C[N+](C)(C)CC1CO1",
"[Cl-]"
]
}
],
[
{
"electron_pushes": [
"lp:N>C_epoxide",
"sigma:C-O>O"
],
"resulting_state": [
"Clc1ccc([NH2+]CC([O-])C)cc1"
]
},
{
"electron_pushes": [
"lp:O>H",
"sigma:N-H>N"
],
"resulting_state": [
"Clc1ccc(NCC(O)C)cc1"
]
}
],
[
{
"electron_pushes": [
"lp:N>C",
"sigma:C-I>I"
],
"resulting_state": [
"CC[N+]1(C2CCCCC2)CCCC1",
"[I-]"
]
}
],
[
{
"electron_pushes": [
"pi:C=C>C",
"sigma:C-H>O",
"pi:C=O>C"
],
"resulting_state": [
"C=C(C)C(CO)C(C)=O"
]
}
],
[
{
"electron_pushes": [
"lp:N>C",
"sigma:C-Br>Br"
],
"resulting_state": [
"[Br-]",
"CCC[N+]1(C)CCCC1"
]
}
],
[
{
"electron_pushes": [
"lp:P>C",
"sigma:C-I>I"
],
"resulting_state": [
"C[P+](OCC)(OCC)OCC",
"[I-]"
]
},
{
"electron_pushes": [
"lp:I>C",
"sigma:C-O>P"
],
"resulting_state": [
"CP(=O)(OCC)OCC",
"CCI"
]
}
],
[
{
"electron_pushes": [
"lp:N>O"
],
"resulting_state": [
"CCOC(=O)c1ccc(-c2cccc[n+]2[O-])cc1",
"CC(=O)O"
]
}
]
],
"methodology": "Classified each reaction: rxns 0,2 = pericyclic (Diels-Alder/hetero-DA), rxns 1,9 = N-oxidation, rxns 3,5,7 = SN2 on alkyl halide by amine, rxn 4 = 2-step epoxide ring opening by amine, rxn 6 = ene reaction, rxn 8 = 2-step Arbuzov. Used target products as final SMILES. Electron pushes follow standard patterns: SN2 = lp+sigma, N-ox = lp, DA = pi+pi+sigma, ene = pi+sigma+pi, epoxide opening = 2x(lp+sigma), Arbuzov = 2x(lp+sigma).",
"final_products": [
"N#CCCC1C=CC=C1",
"[O-][n+]1cccc2ccccc21.CC(=O)O",
"CC1=CCOC(C(C)c2ccccc2)C1",
"C[N+](C)(C)CC1CO1.[Cl-]",
"Clc1ccc(NCC(O)C)cc1",
"CC[N+]1(C2CCCCC2)CCCC1.[I-]",
"C=C(C)C(CO)C(C)=O",
"[Br-].CCC[N+]1(C)CCCC1",
"CP(=O)(OCC)OCC.CCI",
"CCOC(=O)c1ccc(-c2cccc[n+]2[O-])cc1.CC(=O)O"
]
}No trajectory submitted. Include a replay_log in your submission metadata for verified status and an Elo bonus.