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[
{
"name": "IChO-2025_1",
"background": {
"image": "images/1/1_bg.png",
"context": "Sesquiterpenes have the formula C_{15}H_{24}. They are secondary metabolites in plants and both deter insects which eat plants and attract animals which eat the insects. Isocaryophyllene (i-Cy) is a sesquiterpene found in oregano, rosemary, pepper, and cloves. The structural formula of i-Cy can be determined by performing various reactions and analysing the products as shown in the figure."
},
"points": 34
},
{
"name": "IChO-2025_1.1",
"modality": "image + text",
"type": "Structure Construction",
"evaluation": "Structure Match",
"requirement": "",
"points": 7,
"field": "",
"source": "IChO-2025",
"question": {
"context": "Draw the structures of i-Cy, A, and B.",
"image": "images/1/1.1_ques.png",
"requirement": "Convert the drawn structures to SMILES format (stereochemistry not required).",
"parsing_note": "The reaction diagram has been converted to reaction_scheme.",
"reaction_scheme": [
{
"reactant_name": "i-Cy",
"reactant_formula": "C_{15}H_{24}",
"conditions": "H_{2}, Pd/C",
"product_name": "B",
"product_formula": "C_{15}H_{28}"
},
{
"reactant_name": "i-Cy",
"reactant_formula": "C_{15}H_{24}",
"conditions": "(1) BH_{3}/THF (1/3 equiv.), THF ; (2) H_{2}O_{2}, NaOH, H_{2}O",
"product_name": "A",
"product_formula": "C_{15}H_{26}O"
},
{
"reactant_name": "i-Cy",
"reactant_formula": "C_{15}H_{24}",
"conditions": "(1) O_{3}, CH_{2}Cl_{2}; (2) Zn, CH_{3}COOH",
"product_smiles": [
"C=O",
"CC1([C@]([H])(CCC(C)=O)[C@@](C(CCC([H])=O)=O)(C1)[H])C"
]
},
{
"reactant_name": "A",
"reactant_formula": "C_{15}H_{26}O",
"conditions": "(1) O_{3}, CH_{2}Cl_{2}; (2) Zn, CH_{3}COOH",
"product_name": "C",
"product_smiles": "CC1(C)[C@]([C@@]([H])([C@](CO)(CCC([H])=O)[H])C1)([H])CCC(C)=O"
}
]
},
"answer": [
{
"name": "A",
"image": "images/1/1.1_ans_A.png",
"smiles": "CC1=CCC[C@@H](CO)[C@]2([H])[C@]([H])(C(C)(C)C2)CC1",
"alternative_smiles": "CC1=CCCC(CO)C2([H])C([H])(C(C)(C)C2)CC1",
"points": 2,
"grading": {
"partial_credit": [
{
"condition": "if missing a carbon atom in the ring or added another carbon atom in the ring.",
"deduction": -1
}
],
"notes": "Stereochemistry will not be marked for A."
}
},
{
"name": "B",
"image": "images/1/1.1_ans_B.png",
"smiles": "CC1CC[C@@]([H])(C(C)(C)C2)[C@@]2([H])C(C)CCC1",
"alternative_smiles": "CC1CCC([H])(C(C)(C)C2)C2([H])C(C)CCC1",
"points": 2,
"grading": {
"partial_credit": [
{
"condition": "If the structure is incorrect, but consistent with isocaryophyllene (and 2 equivalents of $H_2$ are added).",
"deduction": 0
}
],
"notes": "Also 2 pt Stereochemistry will not be marked for B."
}
},
{
"name": "i-Cy",
"image": "images/1/1.1_ans_i-Cy.png",
"smiles": "C/C(CC[C@]1([H])[C@]2([H])CC1(C)C)=C/CCC2=C",
"alternative_smiles": "C/C(CCC1([H])C2([H])CC1(C)C)=C/CCC2=C",
"points": 3,
"grading": {
"partial_credit": [
{
"condition": "If missing a carbon atom or added another carbon atom in the ring.",
"deduction": -1
},
{
"condition": "If a ring is made by combining two other C atoms and added a methyl to the other carbon",
"deduction": -1
},
{
"condition": "If no second ring is present; only added CH3 to all/one/two carbonyls in the right-hand structure.",
"deduction": -2
}
],
"notes": "The trans-isomer gets full marks. Stereochemistry will not be marked for i-Cy."
}
}
]
},
{
"name": "IChO-2025_1.2",
"modality": "image + text",
"type": "Qualitative Identification",
"evaluation": "Selection Check",
"points": 3,
"field": "",
"source": "IChO-2025",
"question": {
"context": "Circle the stereocentres in compound C and assign them as R or S.",
"image": "images/1/1.2_ques.png",
"parsing_note": "The structure in the image has been converted to SMILES format.",
"smiles": "[H][C@@]1(C(C)(C)C[C@]1([H])[C@@](CCC([H])=O)(CO)[H])CCC(C)=O",
"requirement": "1) Count only carbon atoms (C) in the SMILES string from left to right, ignoring all other atoms like H, O, N. Number each carbon sequentially as C-1, C-2, C-3, etc. 2) Assign R or S configuration to each. Output format: 'C-X: R/S'."
},
"answer": {
"context": "C-1: R, C-6: S, C-7: R",
"image": "images/1/1.2_ans.png",
"grading": {
"partial_credit": [
{
"condition": "Each centre not correctly circled",
"deduction": -1
},
{
"condition": "Each descriptor not correct",
"deduction": -0.5
},
{
"condition": "Each incorrect centre is circled.",
"deduction": -1
}
],
"notes": "Minimum score is 0"
},
"points": 3
}
},
{
"name": "IChO-2025_1.3",
"modality": "image + text",
"type": "Structure Construction",
"evaluation": "Structure Match",
"points": 6,
"field": "",
"source": "IChO-2025",
"question": {
"context": "Clovene (Cv) can be synthesised from i-Cy under acid catalysis. The synthesis of Cv starts from compound D. Draw the structures of compounds E and F.",
"image": "images/1/1.3_ques.png",
"parsing_note": "The reaction diagram has been converted to reaction_scheme.",
"requirement": "Convert the drawn structures to SMILES format (stereochemistry not required).",
"reaction_scheme": [
{
"reactant_name": "D",
"reactant_smiles": "C[C@@]1(CCC2)C=CC(O)[C@@]2(CC(OC)=O)C1",
"conditions": "H^{+} (cat.)",
"product_name": "E",
"product_formula": "C_{12}H_{16}O_{2}"
},
{
"reactant_name": "E",
"reactant_formula": "C_{12}H_{16}O_{2}",
"conditions": "1) LiAlH_{4}, Et_{2}O; 2) H^{+}, H_{2}O",
"product_name": "F"
},
{
"reactant_name": "F",
"step_name": "1",
"product_name": "G",
"product_smiles": "C[C@]1(C=C2)CCC[C@](CCO)(C1)C2=O"
},
{
"reactant_name": "G",
"reactant_smiles": "C[C@]1(C=C2)CCC[C@](CCO)(C1)C2=O",
"step_name": "2",
"product_name": "H",
"product_smiles": "C[C@]1(C=C2)CCC[C@](CC(O)=O)(C1)C2=O"
}
]
},
"answer": [
{
"name": "E",
"image": "images/1/1.3_ans_E.png",
"smiles": "O=C1C[C@@]23C[C@@](CCC3)(C)C=C[C@H]2O1",
"alternative_smiles": "O=C1CC23CC(CCC3)(C)C=CC2O1",
"points": 3,
"grading": {
"partial_credit": [
{
"condition": "If the structure is not cyclic and only the ester is removed.",
"deduction": -2
}
],
"notes": "Stereochemistry will not be marked."
}
},
{
"name": "F",
"image": "images/1/1.3_ans_F.png",
"smiles": "O[C@H]1[C@@]2(CCO)C[C@@](CCC2)(C)C=C1",
"alternative_smiles": "OC1C2(CCO)CC(CCC2)(C)C=C1",
"points": 3,
"grading": {
"partial_credit": [
{
"condition": "If reducing the ester to an aldehyde (and alcohol).",
"deduction": -2
}
],
"notes": "Stereochemistry will not be marked."
}
}
]
},
{
"name": "IChO-2025_1.4-5",
"modality": "image + text",
"type": "Qualitative Identification",
"evaluation": "Selection Check",
"points": 2,
"field": "",
"source": "IChO-2025",
"question": {
"context": "Clovene (Cv) can be synthesised from i-Cy under acid catalysis. The synthesis of Cv starts from compound D. For steps '1' and '2' several reagents could be considered. For example: A. PCC B. K_{2}Cr_{2}O_{7}, H_{2}SO_{4}, H_{2}O C. MnO_{2} D. (i) OsO_{4} , (ii) KHSO_{3} From the reagents above, tick which one(s) would be suitable for step '1'. From the reagents above, tick which one(s) would be suitable for step '2'.",
"image": "images/1/1.4-5_ques.png",
"parsing_note": "The structure in the image has been converted to SMILES format.",
"smiles": {
"name": "PCC",
"components": [
"c1cc[nH+]cc1",
"[O-][Cr](Cl)(=O)=O"
]
},
"requirement": "Convert the drawn structures to SMILES format (stereochemistry not required)."
},
"answer": [
{
"name": "step 1",
"choice": "C",
"points": 1
},
{
"name": "step 2",
"choice": "B",
"points": 1
}
]
},
{
"name": "IChO-2025_1.6",
"modality": "image + text",
"type": "Structure Construction",
"evaluation": "Structure Match",
"points": 8,
"field": "",
"source": "IChO-2025",
"question": {
"context": "Draw the structures of compounds I, J, and K.",
"image": "images/1/1.6_ques.png",
"parsing_note": "The reaction diagram has been converted to reaction_scheme.",
"requirement": "Convert the drawn structures to SMILES format (stereochemistry not required).",
"reaction_scheme": [
{
"reactant_name": "H",
"reactant_smiles": "C[C@]1(C=C2)CCC[C@](CC(O)=O)(C1)C2=O",
"conditions": "1) H_{2}, Pd/C; 2) CH_{3}OH H^{+}",
"product_name": "I"
},
{
"reactant_name": "I",
"conditions": "1) HOCH_{2}CH_{2}OH, H^{+}; 2) NaOH, H_{2}O",
"product_name": "J"
},
{
"reactant_name": "J",
"conditions": "1) SOCl_{2}; 2) Et_{2}CuLi; 3) H^{+}, H_{2}O",
"product_name": "K"
},
{
"reactant_name": "K",
"conditions": "1) NaOH, H_{2}O, Δ",
"intermediate_smiles": "CC1=C2CC[C@]3(CCC[C@]2(CC1=O)C3)C",
"product_name": "Cv",
"product_smiles": "CC1([C@@]2(CC[C@]3(CCC[C@]2(C=C1)C3)C)[H])C"
}
]
},
"answer": [
{
"name": "I",
"image": "images/1/1.6_ans_I.png",
"smiles": "O=C1C=C[C@]2(CCC[C@]1(CC(OC)=O)C2)C",
"alternative_smiles": "O=C1C=CC2(CCCC1(CC(OC)=O)C2)C",
"points": 3,
"grading": {
"partial_credit": [
{
"condition": "if double bond is not reduced.",
"deduction": -2
},
{
"condition": "if ester is not formed",
"deduction": -1
}
],
"notes": "Stereochemistry will not be marked for I. Minimum score is 0 pt."
}
},
{
"name": "J",
"image": "images/1/1.6_ans_J.png",
"smiles": "CC1CC[C@@]([H])(C(C)(C)C2)[C@@]2([H])C(C)CCC1",
"alternative_smiles": "CC1CCC([H])(C(C)(C)C2)C2([H])C(C)CCC1",
"points": 2,
"grading": {
"partial_credit": [
{
"condition": "if acetal group is incorrect/not present.",
"deduction": -1
},
{
"condition": "if original ester is still present; protective group is in place.",
"deduction": -1
},
{
"condition": "if ester is formed with ethylene glycol.",
"deduction": -1.5
}
],
"notes": "Stereochemistry will not be marked for I. Minimum score is 0 pt."
}
},
{
"name": "K",
"image": "images/1/1.6_ans_K.png",
"smiles": "O=C1C=C[C@]2(CCC[C@]1(CC(CC)=O)C2)C",
"alternative_smiles": "O=C1C=CC2(CCCC1(CC(CC)=O)C2)C",
"points": 3,
"grading": {
"partial_credit": [
{
"condition": "If acetal protecting group is still present.",
"deduction": -1
},
{
"condition": "If acid is turned into acid chloride and protective group is removed.",
"deduction": -2
},
{
"condition": "If five-membered ring is already formed with an alcohol group still present.",
"deduction": -2
}
],
"notes": "Stereochemistry will not be marked for I. Minimum score is 0 pt."
}
}
]
},
{
"name": "IChO-2025_1.7-8",
"modality": "image + text",
"type": "Structure Construction",
"evaluation": "Structure Match",
"points": 4,
"field": "",
"source": "IChO-2025",
"question": {
"context": "Humulene (Hu) is another sesquiterpene. It can be converted to α-caryophyllene alcohol (α-Ca), which is similar in structure to Cv. This conversion is an acid-catalysed hydration reaction which takes place via multiple intermediate structures. Incomplete structures of some intermediates, X and Y, are shown. The transformation from Hu to X is an acid-catalysed isomerisation reaction. Intermediate Y is charged.",
"image": "images/1/1.7-8_ques.png",
"parsing_note": "The reaction diagram has been converted to reaction_scheme.",
"requirement": "Convert the completed structures to SMILES format.",
"reaction_scheme": [
{
"reactant_name": "Hu",
"reactant_smiles": "CC1(C)C/C=C(C)/CC/C=C(C)/C/C=C/1",
"conditions": "H^{+} (cat.)",
"product_name": "X",
"product_smiles": "CC1CCC(C)(C)CCC(C)CCC1"
},
{
"reactant_name": "X",
"reactant_smiles": "CC1CCC(C)(C)CCC(C)CCC1",
"conditions": "+H^{+}",
"product_name": "Y",
"product_smiles": "CC1(CC2C3(C)CCCC(C)C3C2C1)C"
},
{
"reactant_name": "Y",
"reactant_smiles": "CC1(CC2C3(C)CCCC(C)C3C2C1)C",
"conditions": "1) H_{2}O, -H^{+}",
"product_name": "α-Ca",
"product_smiles": "CC1(C)CC(C2C1)C3(CCCC2(C3O)C)C"
}
]
},
"answer": [
{
"name": "X",
"image": "images/1/1.7-8_ans_X.png",
"smiles": "CC1=C\\CC/C(C)=C/CC(C)(C)C/C=C/1",
"alternative_smiles": "C/C1=C/C=C/C(C)(C)C/C=C(C)/CCC1",
"points": 2,
"grading": {
"partial_credit": [
{
"condition": "for each mistake down to zero.",
"deduction": -1
},
{
"condition": "if all double bonds are mirrored.",
"deduction": -1
}
]
}
},
{
"name": "Y",
"image": "images/1/1.7-8_ans_Y.png",
"smiles": "CC1(C)CC2C3(CCC[C+](C3C2C1)C)C",
"points": 2,
"grading": {
"partial_credit": [
{
"condition": "if any other charge or group has been added to the structure.",
"deduction": -2
}
]
}
}
]
},
{
"name": "IChO-2025_1.9",
"modality": "image + text",
"type": "Qualitative Identification",
"evaluation": "Selection Check",
"points": 2,
"field": "",
"source": "IChO-2025",
"question": {
"context": "Five carbon atoms are circled in Hu. Through understanding the mechanism we can determine where these five carbon atoms end up in α-Ca. Circle the five corresponding carbon atoms in α-Ca which are circled in Hu.",
"image": [
{
"Hu": "images/1/1.9_ques_Hu.png"
},
{
"Y": "images/1/1.9_ques_α-Ca.png"
}
],
"smiles": {
"Hu": "CC1(C)CC/C=C(C)/CC/C=C(C)/C/C=C/1",
"Y": "CC1(CC(C2(C)CCCC3(C)C2O)C3C1)C"
},
"parsing_note": "The structure in the image has been converted to SMILES format.",
"requirement": "1) Count only carbon atoms (C) in the SMILES string from left to right, ignoring all other atoms like H, O, N. Number each carbon sequentially as C-1, C-2, C-3, etc. 2) In Hu, C-6, C-7, C-12, C-14, C-15 are circled based on Hu smiles. 2) Give the five corresponding carbon atoms in α-Ca which are circled in Hu, Output format: 'C-X, C-X'."
},
"answer": {
"context": "C-5, C-6, C-8, C-12, C-13",
"image": "images/1/1.9_ans.png",
"grading": {
"partial_credit": [
{
"condition": "if five circles are correct.",
"deduction": 0
},
{
"condition": "if four circles are correct and one incorrect or missing.",
"deduction": -1
},
{
"condition": "for more than five carbons circled or two or more incorrect/missing.",
"deduction": -2
}
],
"notes": "Minimum score is 0"
},
"points": 2
}
}
]
|