mechanistic-easy

Score Breakdown

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{
  "steps": [
    [
      {
        "electron_pushes": [
          "lp:N>C",
          "sigma:C-Br>Br"
        ],
        "resulting_state": [
          "[Br-]",
          "CCC[N+]1(C)CCCC1"
        ]
      }
    ],
    [
      {
        "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": [
          "pi:diene_1>sigma",
          "pi:diene_2>sigma",
          "sigma:dienophile>pi"
        ],
        "resulting_state": [
          "N#CCCC1C=CC=C1"
        ]
      }
    ],
    [
      {
        "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>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-Cl>Cl"
        ],
        "resulting_state": [
          "C[N+](C)(C)CC1CO1",
          "[Cl-]"
        ]
      }
    ],
    [
      {
        "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-I>I"
        ],
        "resulting_state": [
          "CC[N+]1(C2CCCCC2)CCCC1",
          "[I-]"
        ]
      }
    ],
    [
      {
        "electron_pushes": [
          "lp:N>O"
        ],
        "resulting_state": [
          "[O-][n+]1cccc2ccccc21",
          "CC(=O)O"
        ]
      }
    ],
    [
      {
        "electron_pushes": [
          "lp:N>O"
        ],
        "resulting_state": [
          "CCOC(=O)c1ccc(-c2cccc[n+]2[O-])cc1",
          "CC(=O)O"
        ]
      }
    ]
  ],
  "methodology": "Classified each reaction by type: Reactions 0,5,7 are SN2 (amine/N attacks alkyl halide, halide leaves). Reaction 1 is carbonyl-ene (formaldehyde as enophile). Reaction 2 is Diels-Alder [4+2] cycloaddition. Reaction 3 is Arbuzov (2-step: P attacks methyl iodide SN2, then I demethylates phosphonium). Reaction 4 is epoxide ring opening by amine (2-step: nucleophilic attack then proton transfer). Reaction 6 is hetero Diels-Alder with Danishefsky diene. Reactions 8,9 are N-oxidation of aromatic N by peracetic acid.",
  "final_products": [
    "[Br-].CCC[N+]1(C)CCCC1",
    "C=C(C)C(CO)C(C)=O",
    "N#CCCC1C=CC=C1",
    "CP(=O)(OCC)OCC.CCI",
    "Clc1ccc(NCC(O)C)cc1",
    "C[N+](C)(C)CC1CO1.[Cl-]",
    "CC1=CCOC(C(C)c2ccccc2)C1",
    "CC[N+]1(C2CCCCC2)CCCC1.[I-]",
    "[O-][n+]1cccc2ccccc21.CC(=O)O",
    "CCOC(=O)c1ccc(-c2cccc[n+]2[O-])cc1.CC(=O)O"
  ]
}