A derivative of this compound with three methyl and carboxyl groups is used for molecular recognition studies and readily coordinates the uranyl ion. Three equivalents of this molecule are bonded to phosphorus to form a ligand with a 170-degree cone angle that is found in both Crabtree’s and Grubbs’ catalysts. 1.74 kilocalories-per-mole is assigned to methyl under the (*) A-value scale used to assess the stability of this molecule’s derivatives. Two doubly-linked Newman projections may be used to visualize unfavorable flagpole interactions that destabilize this molecule’s boat conformation, causing its chair conformation to be favored. This compound is industrially produced by using Raney nickel to hydrogenate benzene. For 10 points, name this cyclic alkane with the formula C6H12. ■END■
| 2025 PLAYTIME Online | 04/26/2025 | Y | 9 | 67% | 0% | 67% | 91.00 |
| 2024 PLAYTIME @ Harvard | 04/26/2025 | Y | 4 | 75% | 0% | 25% | 98.67 |
| 2024 PLAYTIME @ Virginia Tech | 07/11/2025 | Y | 3 | 100% | 0% | 33% | 97.67 |
| 2024 PLAYTIME @ UBC | 10/05/2024 | Y | 8 | 100% | 0% | 0% | 82.50 |
| 2024 PLAYTIME @ WashU | 10/12/2024 | Y | 6 | 100% | 0% | 50% | 98.83 |
| 2024 PLAYTIME @ JHU | 10/26/2024 | Y | 8 | 75% | 0% | 25% | 102.17 |
| 2025 PLAYTIME @ Sheffield | 12/10/2024 | Y | 1 | 100% | 0% | 100% | 117.00 |
| 2025 PLAYTIME @ Northwest | 12/10/2024 | Y | 4 | 50% | 0% | 50% | 93.00 |
| 2025 PLAYTIME @ Claremont | 12/10/2024 | Y | 5 | 100% | 0% | 60% | 101.80 |
| 2025 PLAYTIME @ Florida | 12/10/2024 | Y | 2 | 100% | 0% | 0% | 84.00 |
| 2025 PLAYTIME @ Florida | 12/10/2024 | Y | 1 | 100% | 0% | 0% | 77.00 |
| 2025 PLAYTIME @ CWRU | 12/10/2024 | Y | 3 | 67% | 0% | 33% | 85.00 |
| 2025 PLAYTIME @ Sheffield | 12/10/2024 | Y | 5 | 100% | 0% | 40% | 102.40 |
| Player | Team | Opponent | Buzz Position | Value |
|---|---|---|---|---|
| Theenash Sengupta | MSJ | Goober Gang | 38 | -5 |
| Vincent Du | 4 quizbowl pros go Virginia on North Carolina | Ashurbanipal’s Drag Race | 40 | -5 |
| Daniel Ma | Trip-Hop Quizzer Tricky | Mike Dukakis Tank Battalion | 40 | -5 |
| Euan McCubbin | UW A | Alberta | 45 | -5 |
| Shahar Schwartz | Egypt Airlines Haters | Free Agents 1 | 46 | -5 |
| George Matsumura | UW B | Carleton | 48 | -5 |
| Ameya Bhalerao | mongeese | 2 Italians, 2 Poles, All Noles | 49 | -5 |
| Emmett Cho | Chicago B | Illinois C | 50 | -5 |
| Stan | Gruh | Auburn 2026 | 51 | -5 |
| Joy An | Harvard | Brandeis | 57 | -5 |
| Tony Chen | Toronto B | Guelph | 62 | 10 |
| Arjun Bothra | Haverford A | Rutgers | 62 | -5 |
| Charlie Ruff | McGill B | Toronto C | 64 | 10 |
| Liam Kusalik | Waterloo A | Mac A | 64 | 10 |
| Kunaal Chandrashekar | Toronto A | Toronto D | 65 | 10 |
| Akshay Seetharam | Claremont A | Claremont B | 67 | 10 |
| Yashwanth Bajji | Michigan A | Michigan B | 68 | -5 |
| Bryan Ugaz | Arizona State University A | Washington Connections | 69 | 10 |
| Eric Mukherjee | Mike Dukakis Tank Battalion | Trip-Hop Quizzer Tricky | 70 | 10 |
| Aditya Shivaswamy | Johns Hopkins A | CWRU | 72 | 10 |
| Fish Tsai | girl 15 whale i mean they | P.C.‚ Daniel‚ Michel‚ and Jason B | 77 | -5 |
| Bill Zhao | Keeping Up With the Cardassians | Project2025BC: Make Assyria Great Again | 77 | 10 |
| Alex Xu | Caltech | Art of Premature Signaling | 77 | -5 |
| Chris Yoo | Mahjonng Masters | we need new names | 80 | 10 |
| Victor Prieto | Monsieur Hulot's Academic Team | evil women enjoyers | 80 | 10 |
| Logan Mathis | SIUE | WashU Squirtle | 80 | -5 |
| Neal Joshi | WashU Bulbasaur | Truman State | 81 | 10 |
| Billy Beyer | Billy's Bastion | Qin Shi Huang's Immortality Poison | 82 | 10 |
| Jacob Finley | Notre Dame + Epic Games | Quatumvirate | 82 | 10 |
| Ariel Faeder | Pittsburgh | Oberlin | 84 | 10 |
| Graham Cope | Too much from you lately | Edwin Laundrorat's Long-Lost Man Unclothès Rat Degrosses | 86 | 10 |
| Yrwin Batan | MIT | RIT | 86 | 10 |
| Rhys Lewis | Sheffield A | Sheffield B | 86 | -5 |
| Adsayan Ganesh | Warwick B | Cambridge | 86 | 10 |
| Andy Huff | LSE | Imperial A | 86 | 10 |
| Robert Crawley | Warwick A | Lancaster | 86 | -5 |
| Ryan Rosenberg | Adrianne Lenker 4 Nobel Lit Prize 2K65 | Even in Blacksburg There I Am | 86 | 10 |
| Calvin Bostleman | Ohio State A | Ohio State B | 86 | 10 |
| Edward Li | Johns Hopkins B | Haverford B | 86 | 10 |
| Braden Booth | Missouri | Illinois A | 86 | 10 |
| Yash Mandavia | Illinois B | WashU Charmander | 86 | -5 |
| Conor Thompson | Iowa State | Chicago A | 87 | 10 |
| Caleb Ott | Waterloo B | Waterloo C | 88 | 10 |
| Asha Basu | McGill A | Ottawa A | 89 | 10 |
| Isaac Mammel | Maryland A | Georgetown | 90 | -5 |
| Jacob Egol | Master and Margaritaville | Somehow Paula Deen Returned | 90 | 10 |
| Kethan Raman | UCLA A | UCLA B | 92 | -5 |
| Eloise Wood | Imperial B | Birmingham | 93 | -5 |
| Bhaskar Moorthy | Four Generalists in Search of a Power | Illinois Orange | 93 | -5 |
| Ian Tullis | Art of Premature Signaling | Caltech | 97 | 10 |
| Nikhil Nair | BU | Belmont | 105 | 10 |
| Mason Yu | Brown | Lexington | 105 | 10 |
| Marleyna Parrett | George Mason C | George Mason A | 105 | 10 |
| Kai Madgwick | Manchester | Sheffield C | 107 | 10 |
| Athan Juritsch | Toronto E | Toronto Metropolitan | 111 | 10 |
| Jack Piros | Illinois C | Chicago B | 111 | 10 |
| June Yin | WashU Squirtle | SIUE | 111 | 10 |
| Gary Lin | UCSD | UCSB | 112 | 10 |
| Andrew Nucci | UCLA B | UCLA A | 116 | 10 |
| Sam Hastings | Birmingham | Imperial B | 116 | 10 |
| Daniel Carlton | George Mason B | Catholic University of America | 116 | 10 |
| Jason Cheng | P.C.‚ Daniel‚ Michel‚ and Jason B | girl 15 whale i mean they | 117 | 10 |
| Chris Dech | Brandeis | Harvard | 117 | 0 |
| Laura Bullock | Sheffield B | Sheffield A | 117 | 10 |
| Eoin Neale | Lancaster | Warwick A | 117 | 10 |
| Kevin Ye | Simon Fraser | UBC | 117 | 10 |
| Matt Weiner | Ashurbanipal’s Drag Race | 4 quizbowl pros go Virginia on North Carolina | 117 | 10 |
| Reed Sexton | Michigan B | Michigan A | 117 | 0 |
| Vinayak Singh Bhadoriya | NYU B | George Washington | 117 | 10 |
| Zaid Asif | NYU C | Maryland B | 117 | 0 |
| Gus Vanskike | Maryland B | NYU C | 117 | 0 |
| Kushal Aluru | Rutgers | Haverford A | 117 | 10 |
| Tad Horomanski | 2 Italians, 2 Poles, All Noles | mongeese | 117 | 0 |
| John John Groger | WashU Charmander | Illinois B | 117 | 10 |
| Bennett Grappone | Alberta | UW A | 117 | 10 |
| James O'Reilly | Arizona State University B | South Dakota School of Mines | 117 | 0 |
| Olin Bose | Free Agents 1 | Egypt Airlines Haters | 117 | 10 |
| Akshath Sivachidhambaram | Illinois Orange | Four Generalists in Search of a Power | 117 | 10 |
| TJ Pickering | Goober Gang | MSJ | 117 | 0 |
| Henry Bylinowski | Auburn 2026 | Gruh | 117 | 0 |