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 |
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