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|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Complete the following reactions and select the major products by considering the steric hindrance, and the stability of the products.
2-ethyl-2,6-dimethylcyclohexan-1-one + ethyl acrylate (t-BuOK) ---> A
1-nitropropane + (KOH, (E)-but-2-enenitrile, H2O) ---> B | {
"label": [
"A",
"B",
"C",
"D"
],
"text": []
} | gpqa | gpqa_110 | [
{
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"role": "system"
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{
"content": "HERE IS YOUR CONSTRAINT: You must express ALL of your intermediate reasoning — every step of your analysis, every comparison between options, every deduction — using ONLY s... | wingdings | [
"☞ A: 2-ethyl-2,6-dimethylcyclohexan-1-one + ethyl acrylate → (t-BuOK) → Michael addition → enolate formation at α-carbon of ketone \n□ → ketone with α-tertiary carbon (no α-H at C2) → ✗ (no enolate at C2) \n○ → but enolate possible at C6 (methyl group, less hindered) → C6-H deprotonation → enolate ↑ \n→ conjuga... | [
{
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0.13263639333551125
] | ||
A benzene ring has a carboxylic acid a carbaldehyde and a cyano group all meta to one another. Ortho to the carboxylic acid are a hydroxyl and a dimethyl amino and para to the carboxylic acid is a methoxy group. The methoxy and the alcohol are also both ortho to the nitrile. What is the correct IUPAC name for this mole... | {
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"A",
"B",
"C",
"D"
],
"text": []
} | gpqa | gpqa_42 | [
{
"content": "You are a helpful assistant that will answer the questions given by the user.",
"role": "system"
},
{
"content": "HERE IS YOUR CONSTRAINT: You must express ALL of your intermediate reasoning — every step of your analysis, every comparison between options, every deduction — using ONLY s... | wingdings | [
"● benzene ring (C₆H₆) ◎ \n↓ \n✿ substituents: \n- COOH (carboxylic acid) ■ \n- CHO (carbaldehyde) □ \n- CN (cyano) ● \n→ all meta to one another: \n■ --(meta)-- □ --(meta)-- ● --(meta)-- ■ ✅ ↔ △ (1,3,5-trisubstituted) ✓ \n\n✿ positions: assign COOH at position 1 \n→ COOH = 1 ✅ \n→ meta to COOH: positions... | [
{
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0.1939451277199622
] | ||
A spin-half particle is in a linear superposition 0.5|\uparrow\rangle+sqrt(3)/2|\downarrow\rangle of its spin-up and spin-down states. If |\uparrow\rangle and |\downarrow\rangle are the eigenstates of \sigma{z} , then what is the expectation value up to one decimal place, of the operator 10\sigma{z}+5\sigma_{x} ? Here,... | {
"label": [
"A",
"B",
"C",
"D"
],
"text": []
} | gpqa | gpqa_2 | [
{
"content": "You are a helpful assistant that will answer the questions given by the user.",
"role": "system"
},
{
"content": "HERE IS YOUR CONSTRAINT: You must express ALL of your intermediate reasoning — every step of your analysis, every comparison between options, every deduction — using ONLY s... | wingdings | [
"□: |ψ⟩ = 0.5|↑⟩ + (√3)/2|↓⟩ \n●: ⟨ψ|ψ⟩ = (0.5)² + ((√3)/2)² = 0.25 + 0.75 = 1 ✓ ⇒ normalized \n\nσ_z: |↑⟩ ↦ +1, |↓⟩ ↦ -1 ⇒ σ_z = [[1, 0], [0, -1]] \nσ_x: |↑⟩ ↔ |↓⟩ ⇒ σ_x = [[0, 1], [1, 0]] \n\n⟨σ_z⟩ = ⟨ψ|σ_z|ψ⟩ \n|ψ⟩ = [0.5, √3/2]^T \nσ_z|ψ⟩ = [0.5, -√3/2]^T \n⟨ψ|σ_z|ψ⟩ = (0.5)(0.5) + (√3/2)(-√3/2) = 0.25 -... | [
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"content": "You are a helpful assistant that will answer the questions given by the user.",
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0.3973386750608099
] | ||
There has been an outbreak of an viral infectious disease in your city. You have been asked to design a molecular diagnostic kit for quick detection of this retrovirus. How would you go about designing this kit? | {
"label": [
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"B",
"C",
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],
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"role": "system"
},
{
"content": "HERE IS YOUR CONSTRAINT: You must express ALL of your intermediate reasoning — every step of your analysis, every comparison between options, every deduction — using ONLY s... | wingdings | [
"⚠️ QUESTION INCOMPLETE: OPTIONS A, B, C, D NOT PROVIDED ⚠️ \n∴ CANNOT EVALUATE CHOICES SYMBOLICALLY \n▽ WAITING FOR OPTIONS TO BE SUPPLIED \n▭▭▭▭▭▭▭▭▭▭▭▭▭▭▭▭▭ \n☐ A: ? \n☐ B: ? \n☐ C: ? \n☐ D: ? \n∴ HOLD \n✘ NO OPTIONS → ✗ ANALYSIS \n▽ REQUIRES: [A][B][C][D] TO PROCEED \n☛ SUBMIT OPTIONS \n∴ ∅ → ∅ \nA... | [
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] | [
0.26431718061674003
] | ||
Identify compound E in the following reaction scheme.
Compound A, when reacted with HCN, produces compound B.
Compound B, upon reduction with H2 in the presence of Pd, forms compound C.
Compound C, upon reaction with HNO2, forms compound D.
Compound D, upon elimination of an inert gas, forms compound E.
Hints:
a) Compo... | {
"label": [
"A",
"B",
"C",
"D"
],
"text": []
} | gpqa | gpqa_128 | [
{
"content": "You are a helpful assistant that will answer the questions given by the user.",
"role": "system"
},
{
"content": "HERE IS YOUR CONSTRAINT: You must express ALL of your intermediate reasoning — every step of your analysis, every comparison between options, every deduction — using ONLY s... | wingdings | [
"□ → A: ? \nA + HCN → B → cyanohydrin formation → implies A has C=O (carbonyl) \n1750 cm⁻¹ (strong) → typical for C=O stretch → ↑ conjugation? \n1750 → slightly ↑ frequency → suggests aldehyde/ketone, possibly strained or unconjugated \n∴ A contains carbonyl (C=O) ✅ \n\nHint a): A + phosphorous ylide → 1,2-dim... | [
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{
"content": "You are a helpful assistant that will answer the questions given by the user.",
"role": "system"
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{
... | [
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"line_index": 210,
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] | [
0.13073770491803283
] | ||
A methanol solution of (R)-(+)-Limonene is stirred with Pd/C under a Hydrogen atmosphere. After 1 equivalent of hydrogen is consumed, product 1 is isolated as the major product.
1 is treated with 3-chloroperbenzoic acid, forming product 2.
Product 2 is treated with sodium methoxide, forming product 3.
Product 3 is t... | {
"label": [
"A",
"B",
"C",
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],
"text": []
} | gpqa | gpqa_12 | [
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"role": "system"
},
{
"content": "HERE IS YOUR CONSTRAINT: You must express ALL of your intermediate reasoning — every step of your analysis, every comparison between options, every deduction — using ONLY s... | wingdings | [
"(R)-(+)-Limonene → ☞ C₁₀H₁₆ (monoterpene, cyclic, △¹⁰-menthene, chiral, R-config) \nPd/C + H₂ → catalytic hydrogenation \nH₂ (1 equiv) → selective reduction of △ (C=C) \nLimonene has 2 alkenes: endocyclic (△¹) + exocyclic (△⁸(⁹)) \nPd/C + H₂ → prefers endocyclic △¹ (less steric hindrance) → ✓ \n∴ Product 1: (... | [
{
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"line_index": 200,
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... | [
0.1624031419169939
] | ||
You come across an algorithm that gives the following output (written as input -> output):
AGG -> 115
TGCTGA -> 176
What value does ACAGTGACC give? | {
"label": [
"A",
"B",
"C",
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],
"text": []
} | gpqa | gpqa_79 | [
{
"content": "You are a helpful assistant that will answer the questions given by the user.",
"role": "system"
},
{
"content": "HERE IS YOUR CONSTRAINT: You must express ALL of your intermediate reasoning — every step of your analysis, every comparison between options, every deduction — using ONLY s... | wingdings | [
"☞ A: A=1, C=3, G=7, T=20 → ▪ = sum \nAGG → 1+7+7 = 15 ✗ (≠115) \n∴ ▪ ≠ simple atomic sum \n\n☞ B: use nucleotide mass? \nA = 135.13 g/mol (adenine) \nG = 151.13 g/mol (guanine) \nC = 111.10 g/mol (cytosine) \nT = 126.11 g/mol (thymine) \n\nAGG → 135.13 + 151.13 + 151.13 ≈ 437.39 ✗ (≠115) \n∴ ▪ ≠ nucleotid... | [
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}
] | [
0.46564178551583624
] | ||
ChIP-seq on a PFA-fixed sample with an antibody to the IKAROS transcription factor in human B cells followed by next-generation sequencing and standard quality control, alignment and peak-calling steps produced ChIP peaks that disappeared when PFA+DSG fixation was used. Where are we most likely to find such disappearin... | {
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} | gpqa | gpqa_13 | [
{
"content": "You are a helpful assistant that will answer the questions given by the user.",
"role": "system"
},
{
"content": "HERE IS YOUR CONSTRAINT: You must express ALL of your intermediate reasoning — every step of your analysis, every comparison between options, every deduction — using ONLY s... | wingdings | [
"● ChIP-seq: PFA → peaks ✗ PFA+DSG → no peaks \n∴ peaks dependent on fixation type \nPFA: small crosslinker, primarily monoadducts, weak protein-DNA stabilization \nDSG: homo-bifunctional amine-reactive crosslinker, ↑ protein-protein crosslinks \nPFA+DSG: ↑ protein complex stabilization → may mask epitopes or a... | [
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0.08260325406758451
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"Congratulations, you just landed your dream job at one of the top structural biology labs at Stanfo(...TRUNCATED) | {
"label": [
"A",
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],
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} | gpqa | gpqa_127 | [{"content":"You are a helpful assistant that will answer the questions given by the user.","role":"(...TRUNCATED) | wingdings | ["☐ Given: Express reasoning using ONLY symbolic characters \n☐ Goal: Select correct plasmid fo(...TRUNCATED) | [{"endpoint_type":"chat","litellm_function":"acompletion","model":"together_ai/Qwen/Qwen3-235B-A22B-(...TRUNCATED) | [{"cost":0.0049104,"finish_reason":"stop","input_tokens":762,"model":"together_ai/Qwen/Qwen3-235B-A2(...TRUNCATED) | [
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"reaction of solid A with 8 equivalents of gas B forms bright red product C.\nWhen C reacts with 2 e(...TRUNCATED) | {
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} | gpqa | gpqa_69 | [{"content":"You are a helpful assistant that will answer the questions given by the user.","role":"(...TRUNCATED) | wingdings | ["● A = As₂S₃ ▪ B = Cl₂ ▪ C = AsCl₃·3S ▪ D = NH₃ ▪ E = (NH₄)₃AsS₄ ▪ F =(...TRUNCATED) | [{"endpoint_type":"chat","litellm_function":"acompletion","model":"together_ai/Qwen/Qwen3-235B-A22B-(...TRUNCATED) | [{"cost":0.024686200000000002,"finish_reason":"length","input_tokens":551,"model":"together_ai/Qwen/(...TRUNCATED) | [
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t1-wingdings-gpqa-qwen3-235b-a22b-instruct-2507
Wingdings GPQA eval of Qwen3-235B-A22B-Instruct. pass@1: 0%, compliance: 22.5%
Dataset Info
- Rows: 10
- Columns: 14
Columns
| Column | Type | Description |
|---|---|---|
| question | Value('large_string') | No description provided |
| answer | Value('large_string') | No description provided |
| choices | {'label': List(Value('string')), 'text': List(Value('null'))} | No description provided |
| answer_key | Value('large_string') | No description provided |
| task_source | Value('large_string') | No description provided |
| id | Value('large_string') | No description provided |
| formatted_prompt | List({'content': Value('string'), 'role': Value('string')}) | No description provided |
| prompt_variant | Value('large_string') | No description provided |
| response | List(Value('string')) | No description provided |
| formatted_prompt__metadata | List({'endpoint_type': Value('string'), 'litellm_function': Value('string'), 'model': Value('string'), 'raw_prompt': List({'content': Value('string'), 'role': Value('string')}), 'raw_system_prompt': Value('null'), 'request_payload': Value('string')}) | No description provided |
| response__metadata | List({'cost': Value('float64'), 'finish_reason': Value('string'), 'input_tokens': Value('int64'), 'model': Value('string'), 'output_tokens': Value('int64'), 'raw_response': Value('string')}) | No description provided |
| eval_result | List(Value('bool')) | No description provided |
| eval_result__metadata | List({'choice_labels': List(Value('string')), 'confidence': Value('float64'), 'correct_answer': Value('string'), 'extracted_answer': Value('string'), 'extractor': Value('string'), 'full_span': Value('string'), 'line_index': Value('int64'), 'pattern_used': Value('string')}) | No description provided |
| wingdings_compliance | List(Value('float64')) | No description provided |
Generation Parameters
{
"script_name": "wingdings_compliance/academic_eval.py",
"model": "Qwen/Qwen3-235B-A22B-Instruct-2507-tput",
"description": "Wingdings GPQA eval of Qwen3-235B-A22B-Instruct. pass@1: 0%, compliance: 22.5%",
"hyperparameters": {},
"input_datasets": []
}
Usage
from datasets import load_dataset
dataset = load_dataset("reasoning-degeneration-dev/t1-wingdings-gpqa-qwen3-235b-a22b-instruct-2507", split="train")
print(f"Loaded {len(dataset)} rows")
This dataset is tracked in reasoning-degeneration-dev/PROJECT-MANIFEST
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