mechanistic-easy

Score Breakdown

Your Submission

{
  "steps": [
    [
      {
        "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: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": [
          "pi:diene_1>sigma",
          "pi:diene_2>sigma",
          "sigma:dienophile>pi"
        ],
        "resulting_state": [
          "N#CCCC1C=CC=C1"
        ]
      }
    ],
    [
      {
        "electron_pushes": [
          "lp:N>C",
          "sigma:C-I>I"
        ],
        "resulting_state": [
          "CC[N+]1(C2CCCCC2)CCCC1",
          "[I-]"
        ]
      }
    ],
    [
      {
        "electron_pushes": [
          "lp:N>C",
          "sigma:C-Br>Br"
        ],
        "resulting_state": [
          "[Br-]",
          "CCC[N+]1(C)CCCC1"
        ]
      }
    ],
    [
      {
        "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>O"
        ],
        "resulting_state": [
          "CCOC(=O)c1ccc(-c2cccc[n+]2[O-])cc1",
          "CC(=O)O"
        ]
      }
    ],
    [
      {
        "electron_pushes": [
          "lp:N>O"
        ],
        "resulting_state": [
          "[O-][n+]1cccc2ccccc21",
          "CC(=O)O"
        ]
      }
    ]
  ],
  "methodology": "Classified each reaction by type using starting materials, conditions, and n_steps hint. SN2 reactions (4,5,6): nucleophilic amine/phosphine lone pair attacks electrophilic carbon bearing halide leaving group — concerted backside attack with halide departure. Arbuzov (1): 2-step — phosphorus lone pair attacks methyl iodide forming phosphonium salt, then iodide demethylates an O-ethyl group forming phosphonate ester. Epoxide opening (2): 2-step — amine nitrogen attacks less substituted epoxide carbon (SN2-like ring opening), then intramolecular proton transfer from ammonium to alkoxide. Diels-Alder (3): concerted [4+2] cycloaddition of cyclopentadiene with acrylonitrile. Hetero Diels-Alder (7): concerted [4+2] with isoprene as diene and aldehyde as heterodienophile forming dihydropyran. Ene reaction (0): concerted pericyclic — formaldehyde as enophile reacts with allylic C-H of mesityl oxide. N-oxidations (8,9): aromatic nitrogen lone pair attacks electrophilic oxygen of peracetic acid, transferring oxygen to nitrogen.",
  "final_products": [
    "C=C(C)C(CO)C(C)=O",
    "CP(=O)(OCC)OCC.CCI",
    "Clc1ccc(NCC(O)C)cc1",
    "N#CCCC1C=CC=C1",
    "CC[N+]1(C2CCCCC2)CCCC1.[I-]",
    "[Br-].CCC[N+]1(C)CCCC1",
    "C[N+](C)(C)CC1CO1.[Cl-]",
    "CC1=CCOC(C(C)c2ccccc2)C1",
    "CCOC(=O)c1ccc(-c2cccc[n+]2[O-])cc1.CC(=O)O",
    "[O-][n+]1cccc2ccccc21.CC(=O)O"
  ]
}