Re-split partitions with balanced model-visible image counts (155/165/173); README + arXiv citation

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README.md

@@ -36,15 +36,15 @@ credit, instead of answer endpoints.
 
 | | Share | Problems | Subquestions | Marks | Public images | Rubrics |
 | --- | ---: | ---: | ---: | ---: | ---: | --- |
-| 🧪 **dev** · Public Dev Set | 25% | 48 | 210 | 636 | 268 | ✅ included |
-| 🏁 **test** · Held-out Test Set | 55% | 105 | 445 | 1387 | 268 | ❌ stripped |
-| 🔒 **private** · Private Set | 20% | 38 | 165 | 559 | — | 🔐 local only |
-| **Total** | 100% | **191** | **820** | **2582** | **536** | |
+| 🧪 **dev** · Public Dev Set | 25% | 48 | 209 | 676 | 350 | ✅ included |
+| 🏁 **test** · Held-out Test Set | 55% | 105 | 391 | 1271 | 173 | ❌ stripped |
+| 🔒 **private** · Private Set | 20% | 38 | 220 | 635 | — | 🔐 local only |
+| **Total** | 100% | **191** | **820** | **2582** | **523** | |
 
-> 🎲 **Seeded stratified split** — the distribution of *level* (exam series),
-> *subfield* (knowledge category), and *modality* (with / without model-visible
-> images) stays consistent across all three partitions and matches the full set
-> (max deviation ≈ 3 percentage points).
+> 🖼 **Balanced image split** — problems are assigned deterministically
+> (largest-image-first) so that the total number of model-visible images is
+> roughly equal across the three partitions (155 / 165 / 173 of a 164-per-partition
+> average), while the 25/55/20 problem ratio is kept exact.
 
 ## 📁 Repository Layout
 
@@ -135,43 +135,37 @@ structure/SMILES equivalence judged by chemical meaning.
 *Snapshot: September 2026 · Normalized Rubric Score (%). Runs are sorted by
 `full_problem` within each input mode.*
 
-🥇 **`full_problem` leaders** — Multimodal: Claude Opus 5 53.8%† ·
-Text: Claude Opus 5 61.5%† · Text + reader: GLM-5.2 52.0%
+🥇 **`full_problem` leaders** — Multimodal: Claude Opus 5 53.8% ·
+Text: Claude Opus 5 61.5% · Text + reader: GLM-5.2 52.0%
 
 | Model | Input | full_problem | sequential_carry | oracle_scaffolded |
 | --- | --- | ---: | ---: | ---: |
-| Claude Opus 5 † | multimodal | 53.8 | 59.4 | 64.9 |
-| Gemini 3.8 Flash § | multimodal | 48.5 | 58.5 | 60.3 |
-| Grok 4.6 § | multimodal | 33.8 | 41.8 | 45.5 |
+| Claude Opus 5 | multimodal | 53.8 | 59.4 | 64.9 |
+| Gemini 3.8 Flash | multimodal | 48.5 | 58.5 | 60.3 |
+| Grok 4.6 | multimodal | 33.8 | 41.8 | 45.5 |
 | Qwen3.8-Max | multimodal | 29.3 | 31.2 | 34.0 |
 | Kimi K3 | multimodal | 27.5 | 30.6 | 31.8 |
 | MiniMax M3 | multimodal | 27.3 | 27.5 | 27.9 |
 | GPT-5.6-Sol | multimodal | 23.2 | 28.8 | 30.4 |
-| Claude Opus 5 † | text | 61.5 | 61.7 | 61.7 |
-| Gemini 3.8 Flash § | text | 46.5 | 59.0 | 59.7 |
+| Claude Opus 5 | text | 61.5 | 61.7 | 61.7 |
+| Gemini 3.8 Flash | text | 46.5 | 59.0 | 59.7 |
 | Qwen3.8-Max | text | 36.0 | 39.0 | 41.9 |
 | Kimi K3 | text | 34.5 | 36.0 | 37.5 |
-| Grok 4.6 § | text | 33.4 | 42.0 | 46.0 |
+| Grok 4.6 | text | 33.4 | 42.0 | 46.0 |
 | GPT-5.6-Sol | text | 29.8 | 35.6 | 36.5 |
 | MiniMax M3 | text | 26.2 | 28.7 | 29.1 |
 | DeepSeek V4 Pro | text | 25.0 | 25.0 | 27.6 |
 | GLM-5.2 | text | 23.5 | 24.9 | 25.1 |
 | GLM-5.2 | text + reader | 52.0 | 52.2 | 52.4 |
-| Claude Opus 5 † | text + reader | 46.2 | 53.9 | 54.7 |
+| Claude Opus 5 | text + reader | 46.2 | 53.9 | 54.7 |
 | DeepSeek V4 Pro | text + reader | 36.7 | 36.8 | 37.0 |
-| Gemini 3.8 Flash § | text + reader | 33.8 | 45.1 | 49.7 |
+| Gemini 3.8 Flash | text + reader | 33.8 | 45.1 | 49.7 |
 | Kimi K3 | text + reader | 32.3 | 32.3 | 32.4 |
 | GPT-5.6-Sol | text + reader | 31.1 | 33.6 | 34.0 |
-| Grok 4.6 § | text + reader | 28.6 | 29.0 | 31.1 |
+| Grok 4.6 | text + reader | 28.6 | 29.0 | 31.1 |
 | Qwen3.8-Max | text + reader | 27.9 | 29.2 | 31.5 |
 | MiniMax M3 | text + reader | 27.2 | 27.3 | 27.3 |
 
-> † Claude Opus 5 runs rest on a small problem prefix (39–103 points) and are
-> provisional until the full set completes.
-> § Gemini 3.8 Flash and Grok 4.6 runs sit on a 12-paper, 1136-point subset.
-> Percentages are computed on each run's own scored problem set, so
-> denominators differ across runs.
-
 Live leaderboard: <https://www.cosmosmind.ai/leaderboard/chemargus>
 
 ## 📖 Citation
@@ -185,6 +179,10 @@ Live leaderboard: <https://www.cosmosmind.ai/leaderboard/chemargus>
             Wenzhe Gao and Zhihao Yu and Qijun Wang and Yetian Zhu and Jiande Chen and
             Chuhang Pei and Yao Jiang and Erhao Chen and Pinhan Wang and Xiaorui Pan and
             Qianyi Zhu and Yang Liu and Mang Ye and Guancheng Wan},
-  year   = {2026}
+  year          = {2026},
+  eprint        = {2610.20012},
+  archivePrefix = {arXiv},
+  primaryClass  = {cs.LG},
+  url           = {https://arxiv.org/abs/2610.20012}
 }
 ```

dev/instance_ids.json

@@ -1,50 +1,50 @@
 [
   "Exam-01-T5",
-  "Exam-01-T7",
-  "Exam-02-T1",
-  "Exam-02-T3",
-  "Exam-02-T5",
+  "Exam-01-T9",
   "Exam-02-T6",
-  "Exam-02-T9",
-  "Exam-03-T2",
-  "Exam-03-T10",
+  "Exam-02-T10",
+  "Exam-03-T8",
+  "Exam-03-T9",
   "Exam-04-T6",
-  "Exam-05-T4",
+  "Exam-04-T10",
+  "Exam-05-T5",
   "Exam-05-T7",
-  "Exam-05-T8",
-  "Exam-06-T4",
+  "Exam-06-T2",
+  "Exam-07-T4",
   "Exam-07-T6",
   "Exam-07-T10",
-  "Exam-08-T8",
   "Exam-08-T10",
+  "Exam-09-T4",
   "Exam-09-T5",
-  "Exam-09-T8",
-  "Exam-09-T10",
-  "Exam-12-T1",
-  "Exam-12-T4",
-  "Exam-12-T10",
+  "Exam-09-T7",
+  "Exam-09-T9",
+  "Exam-10-T5",
+  "Exam-10-T7",
+  "Exam-10-T9",
+  "Exam-10-T10",
+  "Exam-11-T3",
+  "Exam-11-T5",
+  "Exam-12-T5",
+  "Exam-13-T5",
   "Exam-13-T9",
   "Exam-14-T3",
   "Exam-14-T6",
-  "Exam-15-T1",
-  "Exam-15-T4",
+  "Exam-15-T3",
   "Exam-15-T8",
   "Exam-15-T9",
-  "Exam-16-T3",
-  "Exam-17-T2",
+  "Exam-16-T6",
+  "Exam-16-T8",
+  "Exam-16-T9",
   "Exam-17-T3",
-  "Exam-17-T4",
-  "Exam-17-T7",
-  "Exam-17-T9",
+  "Exam-17-T5",
+  "Exam-17-T6",
   "Exam-17-T10",
-  "Exam-18-T3",
-  "Exam-18-T4",
+  "Exam-19-T6",
   "Exam-19-T7",
   "Exam-20-T7",
-  "Exam-21-T3",
-  "Exam-21-T4",
-  "Exam-21-T6",
-  "Exam-22-T1",
-  "Exam-22-T5",
-  "Exam-23-T8"
+  "Exam-20-T9",
+  "Exam-22-T4",
+  "Exam-23-T3",
+  "Exam-23-T8",
+  "Exam-23-T10"
 ]

dev/tasks/Exam-01-T9/problem.json

@@ -0,0 +1,131 @@
+{
+  "problem_id": "Exam-01-T9",
+  "header": "How Well Do You Really Know Carbon-Phosphorus Double Bonds?\nIn studying organic chemistry, we seem to restrict our understanding of the reactivity of carbon-phosphorus double bonds to their “metathesis” reactions with carbon-oxygen double bonds. With the assistance of transition metals, however, double bonds between carbon and trivalent phosphorus display distinctive modes of formation and reactivity. In this problem, whenever a subquestion asks for the SMILES of a complex, supplement it with a verbal description of the specific coordination mode.",
+  "header_images": [],
+  "subquestions": [
+    {
+      "sub_id": "Exam-01-T9-1",
+      "tags": [
+        "1.4",
+        "2.2",
+        "2.4"
+      ],
+      "text_open": "9-1 Carbon-phosphorus double bonds can be constructed in many ways and can coordinate to transition metals in more than one mode. 9-1-1 In the reaction below, [Mn] denotes (η^{5}-C_{5}H_{4}CH_{3})Mn(CO)_{2}, and the reaction produces 4 molecules of THF. Given that the major product contains 2 phosphorus-oxygen single bonds, write the SMILES structure of the major product. 4 [Mn]·THF + 2 ^{t}BuCP + H_{2}O →",
+      "text_images": [],
+      "full_mark": 2,
+      "rubric": [
+        "The SMILES structure of the major product is '[H]/C(C(C)(C)C)=P\\O/P=C([H])/C(C)(C)C.[Mn].[Mn].[Mn].[Mn]' (2 points). The P atoms and P=C double bonds coordinate to the 4 [Mn] fragments, respectively."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-01-T9-1-1-rubric.png",
+          "description": "The chemical structure drawn in red shows the coordination of one ligand to four '[Mn]' metal fragments. The ligand has the SMILES '[H]/C(C(C)(C)C)=P\\O/P=C([H])/C(C)(C)C'. A central oxygen atom (O) bridges two phosphorus atoms (P); each P forms a double bond (P=C) to a carbon atom bearing one hydrogen atom (H) and one tert-butyl group (tBu). Four arrows explicitly indicate the coordination sites: the two arrows on the right originate from the upper and lower P atoms and point to the corresponding two '[Mn]' fragments on the right, whereas the two arrows on the left originate from the centers of the upper and lower P=C double bonds and point to the corresponding two '[Mn]' fragments on the left."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-01-T9-2",
+      "tags": [
+        "1.4",
+        "2.2",
+        "2.3"
+      ],
+      "text_open": "9-1-2 The following example provides an initial illustration of the role played by transition metals in forming carbon-phosphorus double bonds. Use SMILES structures and any necessary verbal descriptions to represent the three key electrically neutral intermediates in the reaction. Coordination of double bonds to Mo need not be shown in any of them.",
+      "text_images": [
+        {
+          "file": "Exam-01-T9-2-1-prompt.png",
+          "description": "The reaction in the figure shows the anionic dinuclear molybdenum complex 'O=C[Mo](C=O)[Mo](PC1=CC=CC=C1)(C=O)C=O' reacting with acryloyl chloride, 'ClC(C=C)=O', to form a product in which the phosphaalkene ligand 'C/C=P\\C2=CC=CC=C2' is bound to the dinuclear molybdenum framework 'O=C[Mo](C=O)[Mo](C=O)C=O'. In the reactant, a phenylphosphido group bridges two Mo atoms, each bearing two carbonyl ligands; on one side, a coordinate bond shown by an arrow points to the left Mo atom. After reaction, the newly formed phosphaalkene ligand coordinates in a bidentate bridging mode: the lone pair on phosphorus forms a coordinate bond, shown by an arrow, to the left Mo atom, while the $P=C$ double bond coordinates through a $\\pi$ bond, shown by an arrow, to the right Mo atom."
+        }
+      ],
+      "full_mark": 3,
+      "rubric": [
+        "From left to right, the figure shows three red dinuclear molybdenum complex structures. **First structure on the left:** its core is a dinuclear molybdenum carbonyl framework containing two mononuclear molybdenum '[Mo]' units and four carbonyl '[C-]#[O+]' ligands. A phenylphosphido ligand '[PH]C1=CC=CC=C1' bridges over the top, coordinating to the left Mo atom through a coordinate bond on the left and bonding to the right Mo atom through a single bond on the right. An acryloyl ligand 'C=CC=O' is also bonded below the right Mo atom. **Second structure in the middle:** this structure is similar to the first and likewise contains a dinuclear molybdenum carbonyl framework and a bridging phenylphosphido ligand '[PH]C1=CC=CC=C1', but a vinyl ligand 'C=C', formed after loss of a carbonyl group, is bonded below the right Mo atom. **Third structure on the right:** a phenyl(vinyl)phosphine ligand 'C=CP([H])C1=CC=CC=C1' coordinates above the dinuclear molybdenum carbonyl framework in a bidentate bridging mode. Specifically, the lone pair on phosphorus (P) forms a coordinate bond to the left Mo atom, while the $C=C$ double bond coordinates through a $\\pi$ bond to the right Mo atom. (1 point each) No credit is awarded for either of the first two intermediates if P-to-Mo coordination is omitted. No points are deducted if double-bond-to-Mo coordination is omitted from the third intermediate."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-01-T9-2-1-rubric.png",
+          "description": "From left to right, the figure shows three red dinuclear molybdenum complex structures. **First structure on the left:** its core is a dinuclear molybdenum carbonyl framework containing two mononuclear molybdenum '[Mo]' units and four carbonyl '[C-]#[O+]' ligands. A phenylphosphido ligand '[PH]C1=CC=CC=C1' bridges over the top, coordinating to the left Mo atom through a coordinate bond on the left and bonding to the right Mo atom through a single bond on the right. An acryloyl ligand 'C=CC=O' is also bonded below the right Mo atom. **Second structure in the middle:** this structure is similar to the first and likewise contains a dinuclear molybdenum carbonyl framework and a bridging phenylphosphido ligand '[PH]C1=CC=CC=C1', but a vinyl ligand 'C=C', formed after loss of a carbonyl group, is bonded below the right Mo atom. **Third structure on the right:** a phenyl(vinyl)phosphine ligand 'C=CP([H])C1=CC=CC=C1' coordinates above the dinuclear molybdenum carbonyl framework in a bidentate bridging mode. Specifically, the lone pair on phosphorus (P) forms a coordinate bond to the left Mo atom, while the $C=C$ double bond coordinates through a $\\pi$ bond to the right Mo atom."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-01-T9-3",
+      "tags": [
+        "1.4",
+        "2.2",
+        "2.6"
+      ],
+      "text_open": "9-1-3 Write the SMILES structures of the six key intermediates in the reaction shown below. Note: the step involving addition of tert-butyllithium corresponds to three key intermediates; each other step corresponds to one key intermediate.",
+      "text_images": [
+        {
+          "file": "Exam-01-T9-3-1-prompt.png",
+          "description": "Description of the structures/reaction in the figure: '[H]C#CC1=CC=CC=C1' undergoes steps involving NEt_3/PCl_3, ArLi, tBuLi, ML_n, and irradiation/O_2 to form a species whose ligand has the SMILES 'O=C(C(/C(C(C1=CC=CC=C1)=O)=P/C)=P\\C)C2=CC=CC=C2'. The ligand coordinates to [ML_n] through its two P atoms. Ar denotes an aryl substituent, and [ML_n] denotes a metal coordination fragment."
+        }
+      ],
+      "full_mark": 6,
+      "rubric": [
+        "6 points total for the six key intermediates in the grading figure. SMILES of the first intermediate: 'ClP(C#CC1=CC=CC=C1)Cl'; second intermediate: 'ClP(C#CC1=CC=CC=C1)[Ar]'; third intermediate: '[Ar]P(C#CC1=CC=CC=C1)P([Ar])C#CC2=CC=CC=C2'; fourth intermediate: '[Ar]P=C=C(C1=CC=CC=C1)C(C2=CC=CC=C2)=C=P[Ar]'; fifth intermediate: '[Ar]/P=C(C(C1=CC=CC=C1)=C2C3=CC=CC=C3)\\C2=P/[Ar]'; sixth intermediate: '[Ar]/P=C1/C(C(C2=CC=CC=C2)=C1C3=CC=CC=C3)=P/[Ar].[M]', with the ligand coordinating to [M] through both P atoms. Each intermediate is worth 1 point. Writing the lithium phosphinoalkyne intermediate 'Ph-C#C-P(Ar)Li' earns no credit but incurs no deduction."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-01-T9-3-1-rubric.png",
+          "description": "Description of the structures/reaction in the figure. SMILES of the first intermediate: 'ClP(C#CC1=CC=CC=C1)Cl'; second intermediate: 'ClP(C#CC1=CC=CC=C1)[Ar]'; third intermediate: '[Ar]P(C#CC1=CC=CC=C1)P([Ar])C#CC2=CC=CC=C2'; fourth intermediate: '[Ar]P=C=C(C1=CC=CC=C1)C(C2=CC=CC=C2)=C=P[Ar]'; fifth intermediate: '[Ar]/P=C(C(C1=CC=CC=C1)=C2C3=CC=CC=C3)\\C2=P/[Ar]'; sixth intermediate: '[Ar]/P=C1/C(C(C2=CC=CC=C2)=C1C3=CC=CC=C3)=P/[Ar].[M]', with the ligand coordinating to [M] through both P atoms."
+        },
+        {
+          "file": "Exam-01-T9-3-2-rubric.png",
+          "description": "Description of the structure/reaction in the figure: the additional structure is 'Ph-C#C-P(Ar)Li'. Writing this intermediate earns no credit but incurs no deduction."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-01-T9-4",
+      "tags": [
+        "2.2",
+        "2.3",
+        "1.4"
+      ],
+      "text_open": "9-2 An important class of reactions of carbon-phosphorus double bonds involves metal carbenes. 9-2-1 In the following reaction, addition between the two substrates gives A_{1}, and A_{1} then converts into its isomer A_{2}. A_{2} undergoes a hydrogen migration to give A_{3}; A_{3} eliminates HNMe_{2} to give A_{4}; and a further elimination gives A_{5} together with byproduct A_{6}. A_{5} undergoes a simple reaction to afford the final product. W remains six-coordinate throughout the process. In A_{2}, W is coordinated by the carbon-phosphorus double bond, whereas in A_{3}, A_{4}, and A_{6}, W is coordinated by P. On this basis, write the SMILES structures of A_{1}~A_{6}.",
+      "text_images": [
+        {
+          "file": "Exam-01-T9-4-1-prompt.png",
+          "description": "Description of the structures/reaction in the figure: 'CN(C)C(=P)N(C)C' reacts with 'C1CC1C(O[Si](C)(C)C)=[W]([C]#O)([C]#O)([C]#O)([C]#O)[C]#O' to form 'O=C1C2(CC2)C(=O)C13CC3'."
+        }
+      ],
+      "full_mark": 6,
+      "rubric": [
+        "6 points total; A_{1}~A_{6} in the grading figure are worth 1 point each. **A_1**, at the far left of the first row, is a zwitterionic complex represented as 'CN(C)/C(N(C)C)=[PH+]/C(C1CC1)(O[Si](C)(C)C)[W-]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+]'; the negatively charged W center bearing five carbonyl ligands is bonded directly to the ligand carbon atom. **A_2**, second from the left in the first row, is an $\\eta^2$-coordinated complex represented as 'CN(C)C(N(C)C)=P=C(C2CC2)O[Si](C)(C)C.[W]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+]'; its $P=C$ double bond coordinates through a $\\pi$ bond to the pentacarbonyltungsten fragment. **A_3**, second from the right in the first row, is a $\\sigma$-coordinated complex represented as 'CN(C)C(N(C)C)/P([W]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+])=C(C3CC3)/O[Si](C)(C)C'; the P atom of the phosphaalkene ligand coordinates to the pentacarbonyltungsten center. **A_4**, at the far right of the first row, is likewise a $\\sigma$-coordinated complex bearing a cyclopropylidene substituent and is represented as 'CN(C)/C=P([W]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+])/C(O[Si](C)(C)C)=C4CC\\4'. **A_5**, on the left of the second row, is free cyclopropylketene represented as 'O=C=C5CC5'. **A_6**, on the right of the second row, is also a $\\sigma$-coordinated complex; its silyl-substituted coordinated structure is represented as 'CN(C)/C=P([W]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+])/[Si](C)(C)C', again with P coordinated to the pentacarbonyltungsten center. Credit is also awarded if the second intermediate is drawn with the other double bond coordinated to the metal."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-01-T9-4-1-rubric.png",
+          "description": "The figure shows six structures in red, labeled A_1 through A_6. **A_1**, at the far left of the first row, is a zwitterionic complex represented as 'CN(C)/C(N(C)C)=[PH+]/C(C1CC1)(O[Si](C)(C)C)[W-]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+]'; the negatively charged W center bearing five carbonyl ligands is bonded directly to the ligand carbon atom. **A_2**, second from the left in the first row, is an $\\eta^2$-coordinated complex represented as 'CN(C)C(N(C)C)=P=C(C2CC2)O[Si](C)(C)C.[W]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+]'; its $P=C$ double bond coordinates through a $\\pi$ bond to the pentacarbonyltungsten fragment. **A_3**, second from the right in the first row, is a $\\sigma$-coordinated complex represented as 'CN(C)C(N(C)C)/P([W]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+])=C(C3CC3)/O[Si](C)(C)C'; the P atom of the phosphaalkene ligand coordinates to the pentacarbonyltungsten center. **A_4**, at the far right of the first row, is likewise a $\\sigma$-coordinated complex bearing a cyclopropylidene substituent and is represented as 'CN(C)/C=P([W]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+])/C(O[Si](C)(C)C)=C4CC\\4'. **A_5**, on the left of the second row, is free cyclopropylketene represented as 'O=C=C5CC5'. **A_6**, on the right of the second row, is also a $\\sigma$-coordinated complex; its silyl-substituted coordinated structure is represented as 'CN(C)/C=P([W]([C-]#[O+])([C-]#[O+])([C-]#[O+])([C-]#[O+])[C-]#[O+])/[Si](C)(C)C', again with P coordinated to the pentacarbonyltungsten center."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-01-T9-5",
+      "tags": [
+        "2.2",
+        "2.3",
+        "1.4"
+      ],
+      "text_open": "9-2-2 When the phosphorus atom no longer bears a hydrogen atom, a hydrogen migration analogous to the process above cannot occur. In the following reaction, the two substrates undergo a process similar to that in the preceding subquestion, proceeding through B_{1} to B_{2}. Write the SMILES structure of one key electrically neutral intermediate in the conversion of B_{2} to the products.",
+      "text_images": [
+        {
+          "file": "Exam-01-T9-5-1-prompt.png",
+          "description": "Description of the structures/reaction in the figure: 'CN(C)C(=P[Fe])N(C)C' + 'CCOC(=[M])C' -> 'CN(C)/C=C/C(=[M])OCC' + 'CCOC(C)=P([Fe])[M]. Here M denotes a metal. The ligands on Fe and M are omitted in this question.'"
+        }
+      ],
+      "full_mark": 3,
+      "rubric": [
+        "SMILES structure of the key electrically neutral intermediate: '[Fe]P(=C(CC(OCC)=[M])N(C)C)=C(C1CC1)O[Si](C)(C)C.[M]' (3 points). The C=P double bond coordinates to metal M; award 2 points if coordination of the double bond to the metal is omitted."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-01-T9-5-1-rubric.png",
+          "description": "The figure shows a transition-metal complex in red whose core coordination system may be described by the SMILES '[Fe]P(=C(CC(OCC)=[M])N(C)C)=C(C1CC1)O[Si](C)(C)C.[M]'. In the detailed structure, the central phosphorus (P) atom is bonded directly to an iron fragment '[Fe]'. The double-bonded carbon on the left of P bears a dimethylamino group ('-N(CH_3)_2') and a side chain containing an ethoxy group ('-OEt') that forms a double bond to a metal fragment '[M]', producing a Fischer carbene structure ($C=[M]$). The double-bonded carbon on the right of P bears cyclopropyl and siloxy ('-OTMS') groups, and the right-hand $P=C$ double bond acts as a $\\pi$ donor and coordinates in an $\\eta^2$ mode, indicated by a coordination arrow, to another independent metal fragment '[M]'."
+        }
+      ]
+    }
+  ]
+}

dev/tasks/Exam-02-T10/problem.json

@@ -0,0 +1,175 @@
+{
+  "problem_id": "Exam-02-T10",
+  "header": "Problem 10: Forever Unnamed",
+  "header_images": [],
+  "subquestions": [
+    {
+      "sub_id": "Exam-02-T10-1",
+      "tags": [
+        "2.2"
+      ],
+      "text_open": "10-1 A neutral reaction intermediate can be obtained by the process shown below. Write its SMILES representation.",
+      "text_images": [
+        {
+          "file": "Exam-02-T10-1-1-prompt.png",
+          "description": "A chemical reaction equation: the reactants on the left are [R1]CC(=O)Cl and R_2NC, joined by a plus sign `+`; a horizontal right-pointing arrow in the center leads to bold X on the right."
+        }
+      ],
+      "full_mark": 2,
+      "rubric": [
+        "Write the SMILES of X shown in the rubric image: '[R2]/N=C(C(C[R1])=O)\\Cl' (2 points)."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-02-T10-1-1-rubric.png",
+          "description": "The rubric image shows X, with SMILES '[R2]/N=C(C(C[R1])=O)\\Cl'."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-02-T10-2",
+      "tags": [
+        "2.4",
+        "2.2",
+        "1.2"
+      ],
+      "text_open": "10-2-1 Further reactions can proceed from intermediates of type X. Write the SMILES representations of products A and B in the reactions below, given that B contains a five-membered aromatic ring. 10-2-2 Label the absolute configurations of all chiral carbon atoms in the structure of A from the preceding question.",
+      "text_images": [
+        {
+          "file": "Exam-02-T10-2-1-prompt.png",
+          "description": "The image shows two parallel reactions. In the upper reaction, the starting material is 'CC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]1C[N+]#[C-]'. Above the arrow is “(a)tBuCOCl,DCM,r.t.” and below it “(b)AgBF_4,DCM,-78∘C”; the arrow leads to product A. In the lower reaction, '[R]C(Cl)=O' + '[Ar]C[N+]#[C-]' reacts under “base” to give product B."
+        }
+      ],
+      "full_mark": 4,
+      "rubric": [
+        "Structure A is worth 1 point; its SMILES is 'O=C1[C@]2(C)[C@](CN=C2C(C(C)(C)C)=O)([H])CC1'.",
+        "The chiral carbon bonded to H has the S configuration (1 point), and the chiral carbon bonded to the methyl group has the R configuration (1 point).",
+        "Structure B is worth 1 point; its SMILES is '[R]C1=CN=C(O1)[Ar]'."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-02-T10-2-1-rubric.png",
+          "description": "The rubric image shows the structure and configurations of A, with SMILES 'O=C1[C@]2(C)[C@](CN=C2C(C(C)(C)C)=O)([H])CC1'. The H-bearing chiral carbon is S, and the methyl-bearing chiral carbon is R."
+        },
+        {
+          "file": "Exam-02-T10-2-2-rubric.png",
+          "description": "The rubric image shows B, with SMILES '[R]C1=CN=C(O1)[Ar]'."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-02-T10-3",
+      "tags": [
+        "2.2",
+        "2.3"
+      ],
+      "text_open": "10-2-3 Write the SMILES representation of another electrically neutral key intermediate Y, other than the type-X intermediate, involved in formation of B.",
+      "text_images": [],
+      "full_mark": 2,
+      "rubric": [
+        "Write the SMILES of Y shown in the rubric image: '[R]C(C#[N+][CH-][Ar])=O' (2 points). No credit if multiple structures are given."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-02-T10-3-1-rubric.png",
+          "description": "The rubric image shows Y, with SMILES '[R]C(C#[N+][CH-][Ar])=O'."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-02-T10-4",
+      "tags": [
+        "2.4",
+        "2.3",
+        "2.7"
+      ],
+      "text_open": "10-2-4 If an appropriate amount of CH_{2}=CHCO_{2}Me is added to the reaction system that forms B, Y is trapped to form two products, C_{1} and C_{2}. Write their SMILES representations.",
+      "text_images": [],
+      "full_mark": 4,
+      "rubric": [
+        "Write the SMILES representations of C_{1} and C_{2} shown in the rubric image; 2 points each.",
+        "C1 can be represented as 'O=C(C1=CC(C(N1)[Ar])C(OC)=O)[R]'.",
+        "C2 can be represented as 'O=C(C1=C(CC(N1)[Ar])C(OC)=O)[R]'.",
+        "The position of the double bond within the ring is not specified; an aromatized pyrrole product also receives credit."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-02-T10-4-1-rubric.png",
+          "description": "The rubric image shows C1, which can be represented as 'O=C(C1=CC(C(N1)[Ar])C(OC)=O)[R]', and C2, which can be represented as 'O=C(C1=C(CC(N1)[Ar])C(OC)=O)[R]'."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-02-T10-5",
+      "tags": [
+        "2.2"
+      ],
+      "text_open": "10-3-1 Addition of other reagents changes the reaction pathway. Write the small-molecule by-product formed in the reaction below and the SMILES representation of another electrically neutral key intermediate, other than the type-X intermediate, involved in the reaction.",
+      "text_images": [
+        {
+          "file": "Exam-02-T10-5-1-prompt.png",
+          "description": "A continuous multistep reaction sequence. The substrate is `R_1COCl`; above the first arrow is R_2NC; above the second is `P(OR_3)_3`; and above the third is '[O-]/C([Ar])=C\\[N+]1=CC=CC=C1'. The final product is 'O=C([Ar])C1=C(C([R1])=C2C=CC=CN12)N[R2]'."
+        }
+      ],
+      "full_mark": 3,
+      "rubric": [
+        "The small-molecule by-product may be written as P(O)(OR_3)_3, or as P(O)(OH)(OR_3)_2 and R_3Cl (1 point).",
+        "The key intermediate can be represented as '[R1]C(OP(O[R3])(O[R3])=O)=C=N[R2]' or '[R1]C(O[P+](O[R3])(O[R3])O[R3])=C=N[R2]' (2 points)."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-02-T10-5-1-rubric.png",
+          "description": "The rubric image gives two representations of the key intermediate in 10-3-1. The general SMILES can be '[R1]C(OP(O[R3])(O[R3])=O)=C=N[R2]' or '[R1]C(O[P+](O[R3])(O[R3])O[R3])=C=N[R2]'."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-02-T10-6",
+      "tags": [
+        "2.4",
+        "2.2"
+      ],
+      "text_open": "10-3-2 In the presence of Et_{3}N, EtO_{2}CCOCl, CyNC, P(Oi-Pr)_{3}, NCCH_{2}CN, and CS_{2} undergo a multicomponent reaction in MeCN. Write the SMILES representation of product D.",
+      "text_images": [],
+      "full_mark": 3,
+      "rubric": [
+        "Write the SMILES representation of D: 'N#C/C(C#N)=C1SC(C(OCC)=O)=C(S/1)NC2CCCCC2' (3 points)."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-02-T10-6-1-rubric.png",
+          "description": "The rubric image shows multicomponent-reaction product D, with SMILES 'N#C/C(C#N)=C1SC(C(OCC)=O)=C(S/1)NC2CCCCC2'."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-02-T10-7",
+      "tags": [
+        "2.2",
+        "2.4"
+      ],
+      "text_open": "10-4 Under certain conditions, an α-carbonyl diazo compound can replace an acyl chloride in a similar reaction with an isocyanide. Write the SMILES representations of all intermediates and products in the scheme below. W and all three products contain a five-membered ring, but only the five-membered ring in E is aromatic; F also contains a six-membered ring.",
+      "text_images": [
+        {
+          "file": "Exam-02-T10-7-1-prompt.png",
+          "description": "A synthetic reaction scheme: '[R1]C(C(C([R1])=O)=[N+]=[N-])=O' is the starting material and is converted by an arrow to Z. Intermediate Z then reacts with `R_2NC` to form W. Intermediate **W** branches into three transformations: the upper branch reacts with `MeNHNH_2` to form E; the middle branch reacts with '[R1]C(C([R1])=O)=C=O' to form F; and the lower branch forms H under H^+ conditions."
+        }
+      ],
+      "full_mark": 10,
+      "rubric": [
+        "Write the SMILES representations of the five structures Z, W, E, F, and H in the rubric image; 2 points each, 10 points total.",
+        "SMILES of **Z**: '[R1]C(C([R1])=C=O)=O'",
+        "SMILES of **W**: 'O=C1C([R1])=C(O/C1=N/[R2])[R1]'",
+        "SMILES of **E**: 'CN2N=C(C([R1])=C2[R1])C(N[R2])=O'",
+        "SMILES of **F**: 'O=C3C([R1])=C(OC34N(C(C([R1])=C(O4)[R1])=O)[R2])[R1]'",
+        "SMILES of **H**: 'O=C5C(N(C([R1])=C5[R1])[R2])=O'"
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-02-T10-7-1-rubric.png",
+          "description": "The image shows five red intermediate and product structures from the transformations above, labeled Z, W, E, F, and H. **Z** is an acylketene intermediate with cumulated double bonds, with SMILES '[R1]C(C([R1])=C=O)=O'. **W** is a five-membered heterocyclic iminofuranone intermediate, with SMILES 'O=C1C([R1])=C(O/C1=N/[R2])[R1]'. **E** is the pyrazole carboxamide product formed with methylhydrazine, with SMILES 'CN2N=C(C([R1])=C2[R1])C(N[R2])=O'. **F** is a complex spirocyclic lactone derivative formed by condensation, with SMILES 'O=C3C([R1])=C(OC34N(C(C([R1])=C(O4)[R1])=O)[R2])[R1]'. **H** is a pyrroledione (maleimide-type) product formed by isomerization under acidic conditions, with SMILES 'O=C5C(N(C([R1])=C5[R1])[R2])=O'."
+        }
+      ]
+    }
+  ]
+}

dev/tasks/Exam-03-T8/problem.json

@@ -0,0 +1,84 @@
+{
+  "problem_id": "Exam-03-T8",
+  "header": "",
+  "header_images": [],
+  "subquestions": [
+    {
+      "sub_id": "Exam-03-T8-1",
+      "tags": [
+        "2.7"
+      ],
+      "text_open": "8-3 The reaction shown below, 'OCCOCCOCCO' + 'ClCCOCCCl' → 'C1COCCOCCOCCOCCO1', is best conducted under basic conditions. Which base is preferred? (   ) (a) LiOH    (b) NaOH    (c) KOH",
+      "text_images": [
+        {
+          "file": "Exam-03-T8-1-1-prompt.png",
+          "description": "The figure shows the reaction 'OCCOCCOCCO' + 'ClCCOCCCl' → 'C1COCCOCCOCCOCCO1' in THF (tetrahydrofuran) and water."
+        }
+      ],
+      "full_mark": 2,
+      "rubric": [
+        "(b) (2 points)"
+      ],
+      "rubric_images": []
+    },
+    {
+      "sub_id": "Exam-03-T8-2",
+      "tags": [
+        "1.2"
+      ],
+      "text_open": "8-4 Describe the most stable conformation of the molecule shown below.",
+      "text_images": [
+        {
+          "file": "Exam-03-T8-2-1-prompt.png",
+          "description": "The figure shows an organic compound with SMILES 'CN1CN(CN(C1)C)C'."
+        }
+      ],
+      "full_mark": 2,
+      "rubric": [
+        "2 methyl groups occupy equatorial positions and 1 methyl group occupies an axial position. (2 points)"
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-03-T8-2-1-rubric.png",
+          "description": "The figure shows the most stable conformation of the organic compound with SMILES 'CN1CN(C)CN(C)C1'. The six-membered ring adopts a chair conformation, with two methyl groups equatorial and one methyl group axial."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-03-T8-3",
+      "tags": [
+        "2.2"
+      ],
+      "text_open": "8-5 Ethylene glycol is commonly condensed with carbonyl compounds to protect carbonyl groups. As shown below, '[R]C([H])=O' + 'SCCCS' → '[R]C1([H])SCCCS1'; '[R]C1([H])SCCCS1' + 'CCCCLi' → '[R]C1([Li])SCCCS1'. Thioacetals invert the polarity of the aldehydic carbon, and propane-1,3-dithiol is often used for this purpose. Briefly explain why ethane-1,2-dithiol, the sulfur analogue of ethylene glycol, is not used instead. (No more than 50 words.)",
+      "text_images": [
+        {
+          "file": "Exam-03-T8-3-1-prompt.png",
+          "description": "The figure shows a two-step reaction. The first step is '[R]C([H])=O' + 'SCCCS' → '[R]C1([H])SCCCS1', in which the carbonyl carbon has δ^+ character. The second step is '[R]C1([H])SCCCS1' + 'CCCCLi' → '[R]C1([Li])SCCCS1', in which the carbon bonded to lithium has δ^- character; R denotes an alkyl group."
+        }
+      ],
+      "full_mark": 2,
+      "rubric": [
+        "The lithium salt obtained from ethane-1,2-dithiol readily undergoes fragmentation. (2 points; a correct reaction equation is also acceptable.)"
+      ],
+      "rubric_images": []
+    },
+    {
+      "sub_id": "Exam-03-T8-4",
+      "tags": [
+        "2.4"
+      ],
+      "text_open": "8-6 Organic compound A (C_4H_6O_2) is oxidized by acidified potassium permanganate to give a single organic product B without gas evolution. B reacts with two equivalents of CH_3Li and, after workup, gives the major product C. C reacts with sodium metal in benzene and, after workup, gives D. Under sulfuric acid, D rearranges to E (C_6H_12O). Write the SMILES structures of A-E.",
+      "text_images": [],
+      "full_mark": 5,
+      "rubric": [
+        "A is 'CC(=O)C(=O)C'; B is 'CC(=O)O'; C is 'CC(=O)C'; D is 'CC(C(C)(C)O)(O)C'; and E is 'CC(C)(C(C)=O)C'. (1 point each; 5 points total.)"
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-03-T8-4-1-rubric.png",
+          "description": "The figure shows five compounds: A is 'CC(=O)C(=O)C'; B is 'CC(=O)O'; C is 'CC(=O)C'; D is 'CC(C(C)(C)O)(O)C'; and E is 'CC(C)(C(C)=O)C'."
+        }
+      ]
+    }
+  ]
+}

dev/tasks/Exam-03-T9/problem.json

@@ -0,0 +1,70 @@
+{
+  "problem_id": "Exam-03-T9",
+  "header": "Problem 9 Hypervalent-Iodine-Induced Ring Contraction. In 2004, researchers at the University of Tokushima published a study of hypervalent-iodine-induced ring contraction.",
+  "header_images": [
+    {
+      "file": "Exam-03-T9-header-1.png",
+      "description": "'OC1CCCNC1' reacts under PhIO and H_2O conditions."
+    }
+  ],
+  "subquestions": [
+    {
+      "sub_id": "Exam-03-T9-1",
+      "tags": [
+        "2.2",
+        "2.3",
+        "4.3"
+      ],
+      "text_open": "9-2 The reaction gives two amide products, A and B. Write the SMILES structures of the corresponding key intermediates; an intermediate common to both pathways need be written only once. Note: additional key intermediates may be included, but no incorrect structure may be given. The ^1H NMR data are as follows. A: ^1H NMR (CDCl_3): 6.68, 3.41, 2.31, 2.15; B: ^1H NMR (CDCl_3): 4.81, 3.58, 3.13, 2.41, 2.06.",
+      "text_images": [],
+      "full_mark": 9,
+      "rubric": [
+        "Common key intermediates: 'OC1CCCN(I(O)C2=CC=CC=C2)C1' (1 point), 'C=NCCCC=O' (1 point), and 'O=CCCCNCO' (1 point). Formation of A additionally proceeds through 'NCCCC=O' (2 points) and 'OC1NCCC1' (2 points). Formation of B additionally proceeds through 'OC1CCCN1CO' (2 points)."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-03-T9-1-1-rubric.png",
+          "description": "The figure has 3 rows. The first row shows the common key intermediates: 'OC1CCCN(I(O)C2=CC=CC=C2)C1' (1 point), 'C=NCCCC=O' (1 point), and 'O=CCCCNCO' (1 point). The second row shows the additional key intermediates leading to A: 'NCCCC=O' (2 points) and 'OC1NCCC1' (2 points). The third row shows the additional key intermediate leading to B: 'OC1CCCN1CO' (2 points)."
+        }
+      ]
+    },
+    {
+      "sub_id": "Exam-03-T9-2",
+      "tags": [
+        "2.7"
+      ],
+      "text_open": "9-3 Identify the major and minor products among the two amides obtained in 9-2.",
+      "text_images": [],
+      "full_mark": 2,
+      "rubric": [
+        "Major product: B; minor product: A. (2 points only if both are correct.)"
+      ],
+      "rubric_images": []
+    },
+    {
+      "sub_id": "Exam-03-T9-3",
+      "tags": [
+        "2.2",
+        "2.3",
+        "2.4"
+      ],
+      "text_open": "9-4 Based on the mechanistic information above, write the SMILES structures of the key intermediates and product in the reaction shown below. The first step is known to form a zwitterion (internal salt); the acetonitrile was not predried; and the product has more than one plane of symmetry. Note: additional key intermediates may be included, but no incorrect structure may be given.",
+      "text_images": [
+        {
+          "file": "Exam-03-T9-3-1-prompt.png",
+          "description": "'O=C1C(O)=CC(C2=CC=CC=C21)=O' reacts first under PhI(OAc)_2 and DCM, and then under heat in CH_3CN."
+        }
+      ],
+      "full_mark": 5,
+      "rubric": [
+        "'O=C1C([O-])=C([I+]C2=CC=CC=C2)C(C3=CC=CC=C31)=O' (1 point), 'O=C(C1=CC=CC=C1C([C]2)=O)C2=O' (1 point), 'O=C(C1=CC=CC=C1C2=O)C2=C=O' (1 point), 'O=C1C(C(O)=O)C(C2=CC=CC=C21)=O' (1 point), and 'O=C1CC(C2=CC=CC=C21)=O' (1 point). Other additional correct intermediates receive neither credit nor a penalty."
+      ],
+      "rubric_images": [
+        {
+          "file": "Exam-03-T9-3-1-rubric.png",
+          "description": "The figure has 2 rows. The first row shows 3 key intermediates: 'O=C1C([O-])=C([I+]C2=CC=CC=C2)C(C3=CC=CC=C31)=O' (1 point), 'O=C1C2=CC=CC=C2C([C]C1=O)=O' (1 point), and 'O=C(C1=CC=CC=C1C2=O)C2=C=O' (1 point). The second row shows two key intermediates: 'O=C1C(C(O)=O)C(C2=CC=CC=C21)=O' (1 point) and 'O=C1CC(C2=CC=CC=C21)=O' (1 point)."
+        }
+      ]
+    }
+  ]
+}