This functional group is produced using Kagan’s reagent or samarium(II) iodide in the intramolecular Barbier reaction. This functional group is converted to an alkyl chloride using carbon tetrachloride and tri·phenyl·phosphine in the Appel reaction. This functional group is treated with an azo·di·carboxylate such as DEAD in the Mitsunobu reaction. NMO reoxidizes (*) osmium tetroxide in a reaction named for Upjohn that adds two of these functional groups across an alkene. These functional groups may be treated with tosyl chloride to improve their leaving ability in SN2 reactions, while PCC selectively oxidizes them into carbonyls. Carboxylic acids and this functional group are refluxed together during the Fischer esterification. For 10 points, hydration reactions produce what functional group with the formula -OH? ■END■
| 2025 PLAYTIME Online | 04/26/2025 | Y | 9 | 100% | 11% | 33% | 82.22 |
| 2024 PLAYTIME @ Harvard | 04/26/2025 | Y | 4 | 100% | 25% | 0% | 61.25 |
| 2024 PLAYTIME @ Virginia Tech | 07/11/2025 | Y | 3 | 67% | 0% | 33% | 92.00 |
| 2024 PLAYTIME @ UBC | 10/05/2024 | Y | 8 | 100% | 25% | 0% | 76.63 |
| 2024 PLAYTIME @ WashU | 10/12/2024 | Y | 3 | 100% | 0% | 0% | 75.67 |
| 2024 PLAYTIME @ JHU | 10/26/2024 | Y | 8 | 88% | 0% | 13% | 103.86 |
| 2025 PLAYTIME @ Northwest | 12/10/2024 | Y | 4 | 100% | 25% | 0% | 96.00 |
| 2025 PLAYTIME @ Claremont | 12/10/2024 | Y | 5 | 100% | 0% | 0% | 93.40 |
| 2025 PLAYTIME @ Florida | 12/10/2024 | Y | 3 | 33% | 0% | 67% | 64.00 |
| 2025 PLAYTIME @ CWRU | 12/10/2024 | Y | 5 | 100% | 0% | 20% | 86.80 |
| 2025 PLAYTIME @ Sheffield | 12/10/2024 | Y | 6 | 100% | 0% | 0% | 88.33 |
| Player | Team | Opponent | Buzz Position | Value |
|---|---|---|---|---|
| Bryan Ugaz | Arizona State University A | UW A | 28 | 15 |
| Nikhil Nair | BU | MIT | 33 | 15 |
| Victor Prieto | Monsieur Hulot's Academic Team | Notre Dame + Epic Games | 33 | -5 |
| Alex Li | Free Agents 1 | Illinois Orange | 39 | 15 |
| Athan Juritsch | Toronto E | Waterloo B | 39 | 10 |
| Tracy Mirkin | Edwin Laundrorat's Long-Lost Man Unclothès Rat Degrosses | Keeping Up With the Cardassians | 48 | -5 |
| Eric Mukherjee | Mike Dukakis Tank Battalion | mongeese | 48 | -5 |
| Raymond Chen | Toronto C | Ottawa A | 50 | 15 |
| Liam Kusalik | Waterloo A | UBC | 50 | 15 |
| Shahar Schwartz | Egypt Airlines Haters | we need new names | 51 | -5 |
| Mason Yu | Brown | Brandeis | 52 | 10 |
| Samarth Ram | Chicago B | Iowa State | 61 | 10 |
| Neal Joshi | WashU Bulbasaur | Missouri | 61 | 10 |
| Ryan Rosenberg | Adrianne Lenker 4 Nobel Lit Prize 2K65 | Master and Margaritaville | 63 | -5 |
| Benjamin Chapman | Toronto B | Toronto D | 63 | 10 |
| Derrick Liu | Johns Hopkins B | NYU B | 64 | -5 |
| Shiva Tegulla | Qin Shi Huang's Immortality Poison | Too much from you lately | 64 | 10 |
| Calvin Bostleman | Ohio State A | Oberlin | 65 | 10 |
| Vincent Du | 4 quizbowl pros go Virginia on North Carolina | Even in Blacksburg There I Am | 65 | 10 |
| Kushal Aluru | Rutgers | Maryland B | 68 | 10 |
| Stan | Gruh | MSJ | 68 | 10 |
| Alex Xu | Caltech | UCSD | 68 | 10 |
| Akshay Seetharam | Claremont A | UCLA B | 68 | 10 |
| Eugenia Tong | Imperial A | Lancaster | 68 | 10 |
| Joy An | Harvard | Lexington | 68 | 10 |
| Henry Bylinowski | Auburn 2026 | Mahjonng Masters | 68 | 10 |
| Jacob Finley | Notre Dame + Epic Games | Monsieur Hulot's Academic Team | 68 | 10 |
| Daniel Sheinberg | Trip-Hop Quizzer Tricky | Quatumvirate | 68 | 10 |
| Pranet Sirikonda | Ohio State C | Michigan C | 73 | 10 |
| Bill Zhao | Keeping Up With the Cardassians | Edwin Laundrorat's Long-Lost Man Unclothès Rat Degrosses | 79 | 0 |
| Yashwanth Bajji | Michigan A | Michigan D | 83 | 10 |
| Ted Harrison | Edinburgh | Manchester | 87 | 10 |
| Brendan Bethlehem | Cambridge | Warwick A | 92 | 10 |
| Cade Reinberger | RIT | Belmont | 92 | 10 |
| Arjun Bothra | Haverford A | George Mason C | 92 | 10 |
| Eloise Wood | Imperial B | Sheffield C | 93 | 10 |
| Danny Fisher | Warwick C | Sheffield A | 93 | 10 |
| Saketh Dontaraju | NYU A | Johns Hopkins A | 93 | 10 |
| Seth | Mac A | Simon Fraser | 93 | 10 |
| Biyang Zhang | Michigan B | Pittsburgh | 94 | 10 |
| Asha Basu | McGill A | McGill B | 94 | 10 |
| Adsayan Ganesh | Warwick B | Sheffield B | 97 | 10 |
| Khanh Nguyen | Project2025BC: Make Assyria Great Again | Billy's Bastion | 98 | -5 |
| Fern Fang | evil women enjoyers | Goober Gang | 100 | 10 |
| Daniel Merida | Four Generalists in Search of a Power | 2 Italians, 2 Poles, All Noles | 105 | 10 |
| Payton Chung | girl 15 whale i mean they | UCLA A | 105 | 10 |
| Ameya Bhalerao | mongeese | Mike Dukakis Tank Battalion | 105 | 10 |
| Jason Zhang | Toronto A | Guelph | 105 | 10 |
| Benny Feldman | Chicago A | WashU Charmander | 105 | 10 |
| Ian Tullis | Art of Premature Signaling | Claremont B | 108 | 10 |
| Jacob Goodson | Ohio State B | Ohio State D | 117 | -5 |
| Andy Yu | Maryland A | Georgetown | 118 | 10 |
| Matthew Bucek | George Mason A | NYU C | 118 | 10 |
| George Matsumura | UW B | Arizona State University B | 118 | 10 |
| Parikshit Chauhan | P.C.‚ Daniel‚ Michel‚ and Jason B | UCSB | 118 | 10 |
| Alyx Reckanh | Billy's Bastion | Project2025BC: Make Assyria Great Again | 118 | 0 |
| Vinayak Singh Bhadoriya | NYU B | Johns Hopkins B | 119 | 10 |
| Liam Markland | Alberta | Washington Connections | 119 | 0 |
| Padraig Finan | Washington Connections | Alberta | 119 | 10 |
| Aaron Marchand | Carleton | SD Mines | 119 | 10 |
| Sky Hong | we need new names | Egypt Airlines Haters | 119 | 10 |
| Jacob Egol | Master and Margaritaville | Adrianne Lenker 4 Nobel Lit Prize 2K65 | 119 | 10 |
| Subhamitra Banerjee Roychoudhury | Somehow Paula Deen Returned | Ashurbanipal’s Drag Race | 119 | 0 |
| Matt Weiner | Ashurbanipal’s Drag Race | Somehow Paula Deen Returned | 119 | 0 |
| Aditya Patnaik | Ohio State D | Ohio State B | 119 | 10 |
| Brayden Whitlow | George Mason B | George Washington | 119 | 0 |
| Luis D'Olhaberriague | George Washington | George Mason B | 119 | 0 |
| Dillon George | Catholic University of America | Haverford B | 119 | 0 |
| Avery Barnett | Haverford B | Catholic University of America | 119 | 10 |
| Dawson Teu | Waterloo C | Toronto Metropolitan | 119 | 10 |