This reaction is followed by bromination and rearrangement steps to generate flavonols in the Auwers synthesis. Proline catalyzes an asymmetric version of this reaction used to generate Hajos-Parrish (“high-OHSH-pare-ish”) ketones for steroid synthesis. This reaction forms citrate from oxalo·acetate and acetyl-CoA in the first step of the TCA cycle. This reaction’s chair-like intermediate determines its stereochemistry according to the (*) Zimmerman-Traxler model. This reaction follows a Michael addition in the mechanism for the Robinson Annulation. Under basic conditions, this reaction’s final step occurs via an E1cB mechanism to form an alpha-beta unsaturated product. For 10 points, name this reaction where an enolate attacks a carbonyl to make a product with both aldehyde and alcohol groups. ■END■
| 2025 Penn Bowl - Stanford | 10/25/25 | Y | 4 | 75% | 25% | 50% | 50.00 |
| 2025 Penn Bowl - Northwestern | 10/25/25 | Y | 4 | 50% | 25% | 50% | 67.50 |
| 2025 Penn Bowl - Mainsite (UPenn) | 11/01/25 | Y | 6 | 83% | 17% | 17% | 77.40 |
| 2025 Penn Bowl - BU | 11/01/25 | Y | 3 | 67% | 33% | 33% | 52.50 |
| 2025 Penn Bowl - CWRU | 11/01/25 | Y | 3 | 0% | 0% | 0% | 0.00 |
| 2025 Penn Bowl - UNC | 11/01/25 | Y | 3 | 33% | 33% | 0% | 39.00 |
| 2025 Penn Bowl - WashU | 11/01/25 | Y | 2 | 0% | 0% | 100% | 0.00 |
| 2025 Penn Bowl - Ottawa | 11/01/25 | Y | 7 | 29% | 14% | 29% | 57.00 |
| 2025 Penn Bowl - UK | 11/01/25 | Y | 8 | 88% | 13% | 25% | 94.71 |
| 2025 Penn Bowl - Online | 11/08/25 | Y | 2 | 50% | 0% | 50% | 106.00 |
| 2025 Penn Bowl - Murray State | 11/08/25 | Y | 1 | 0% | 0% | 100% | 0.00 |
| Player | Team | Opponent | Buzz Position | Value |
|---|---|---|---|---|
| Matthew Schiavone | Northwestern A | Indiana | 22 | 15 |
| Shahar Schwartz | Free Win | Berkeley C | 23 | 15 |
| Aditya Shivaswamy | JHU A | Columbia A | 23 | 15 |
| Vivek Sasse | Hail to the Sheaf | To buzz is to be perceived | 26 | -5 |
| Andrew Wang | Illinois | UChicago C | 28 | -5 |
| Ewan MacAulay | Washed Scrubs | Galactic Ombudsmen | 31 | 15 |
| Caleb Ott | Waterloo you are crooked | Carleton A | 31 | -5 |
| Richard Niu | The best time to buzz was twenty clues ago. The second best time to buzz is now | Berkeley A | 37 | -5 |
| Tony Chen | Toronto G | Toronto Sunshine Bubbles | 39 | 15 |
| Allan Lee | Stanford A | Stanford B | 39 | -5 |
| Ted Warner | Bristold | The Bit and the Penndulum | 39 | -5 |
| Ilyas Choukri | VT A | Planck Sinatra | 39 | 15 |
| June Yin | WashU Kiki | Truman State | 42 | -5 |
| Daniel Ma | Mount Sinai | John Jay | 43 | -5 |
| Jonathan Huang | MIT A | MIT B | 47 | 15 |
| Aatreyo Bhattacharyya | abg academy | rusty shackleford | 49 | -5 |
| Jesse Chusing | #OpenToBuzz | Ottawa 67s | 50 | -5 |
| Mason Yu | Brown | Yale | 58 | 10 |
| Joy An | Harvard | I've been running into you in my lead plumbocene what could have benzene | 58 | -5 |
| Swapnil Garg | Berkeley A | The best time to buzz was twenty clues ago. The second best time to buzz is now | 59 | 10 |
| Neal Joshi | VJ Edgecombe School of Interior Design - Edwardsville | WashU Bouba | 59 | -5 |
| Stephen Liu | In Search of Lost Clues | Berkeley B | 68 | 10 |
| Coby Tran | UChicago B | Northwestern B | 68 | -5 |
| Michael Wu | Coughing Baby | Penn and the Art of Tossup-Bonus cycle Maintenance | 72 | 10 |
| Olin Bose | Columbia B | Maryland C | 72 | 10 |
| Ryan Rosenberg | NYU A | NYU B | 74 | 10 |
| Raymond Chen | Toronto Operation PBSuccess | Aweille Kevin Fan osti continue comme ça | 75 | 10 |
| Jonathan Lau | Maryland A | Swarthmore | 106 | 10 |
| Braxton Davis | New Young Whigs of America | Wake Up Paddington A Washington Mystery | 106 | 10 |
| Brody Sadler | Central Oklahoma | Texas A | 109 | -5 |
| Ethan Webb | Of Mice and Penn | Chimp Brisket | 110 | 10 |
| Daoud Jackson | To buzz is to be perceived | Hail to the Sheaf | 112 | 10 |
| Nathan Long | Quiztian Bale in Ratman Begins | question mark | 112 | 10 |
| Jerry Vinokurov | John Jay | Mount Sinai | 112 | 10 |
| Robert Crawley | Paul Quifford, or, It Was a Dark and Stormy Tournament | Knorr Stock Clue | 113 | 0 |
| Brendan Bethlehem | Knorr Stock Clue | Paul Quifford, or, It Was a Dark and Stormy Tournament | 113 | 10 |
| Eugenia Tong | The Bit and the Penndulum | Bristold | 113 | 10 |
| CT Tang | why is it called a score clue if nobody scores points on it | Alas poor Warwick, I knew him Edinburgh | 113 | 0 |
| Danny Fisher | Alas poor Warwick, I knew him Edinburgh | why is it called a score clue if nobody scores points on it | 113 | 0 |
| Emily Kadolph | VT B | UNC B | 113 | 0 |
| Alma Gazzaniga | UNC B | VT B | 113 | 0 |
| Josh Koch | Michigan B | CWRU | 113 | 0 |
| Pace Klein | CWRU | Michigan B | 113 | 0 |
| Aditya Patnaik | Ohio State A | Michigan C | 113 | 0 |
| Jacob Goodson | Ohio State B | Pittsburgh | 113 | 0 |
| Danny Peelen | Pittsburgh | Ohio State B | 113 | 0 |
| Gus Vanskike | Maryland B | JHU B | 113 | 0 |
| Omer Korkmaz | JHU B | Maryland B | 113 | 0 |
| Christopher Bradley | rusty shackleford | abg academy | 113 | 0 |
| Kevin Le | Carleton A | Waterloo you are crooked | 113 | 0 |
| Franklin Wu | Toronto Murder on the Rider Express | McGill B | 113 | 0 |
| Brendan Bridle | Queen's is monitoring the situation | McGill Fartlets | 113 | 0 |
| Charlie Ruff | McGill Fartlets | Queen's is monitoring the situation | 113 | 0 |
| Alec Zelek | Toronto E | Guelph perfomative male competition | 113 | 0 |
| Eva Mandelbaum | Guelph perfomative male competition | Toronto E | 113 | 0 |
| Bryce Cruise | Texas A | Central Oklahoma | 113 | 0 |
| Owen Eskey | Northwestern B | UChicago B | 113 | 10 |
| Beckett Pursey | Purdue B | UChicago A | 113 | 0 |
| Aden Sun | UChicago A | Purdue B | 113 | 0 |
| Paul Lee | WashU Bouba | VJ Edgecombe School of Interior Design - Edwardsville | 113 | 0 |
| Aditya Sharma | Wise Duke | UNC A | 113 | 0 |
| Nick Smemoe | UNC A | Wise Duke | 113 | 0 |