Question
Gilbert Stork devoted a controversial footnote of their pioneering quinine synthesis to dismissing quinine’s first formal synthesis, which was conducted by this scientist and Robert Woodward. For 10 points each:
[10h] Name this chemist who determined the mechanism of the Baeyer–Villiger oxidation with Edwin Dorfman. This scientist worked with Wolfgang Roth to identify a reaction’s chair transition state.
ANSWER: William Doering [or William von Eggers Doering; accept Doering–Dorfman experiment or Doering–Roth experiment]
[10m] Doering and Roth predicted that bullvalene (“BULL-vuh-leen”) would only have one proton NMR peak because of how rapidly it undergoes this sigmatropic reaction.
ANSWER: Cope rearrangement [prompt on Cope reaction; prompt on rearrangement; reject “Cope elimination”]
[10e] Bullvalene can undergo this many possible rearrangements at any given moment, as each swaps the bridgehead carbon with a cyclopropyl (“cyclo-PRO-pill”) carbon. There are this many carbons in propane.
ANSWER: three [or 3]
<Chemistry>
Summary
| 2024 ACF Nationals | 2024-04-21 | Y | 24 | 11.67 | 92% | 25% | 0% |
Data
| Rutgers | Arizona State | 0 | 10 | 10 | 20 |
| Michigan | Brown | 0 | 0 | 10 | 10 |
| Chicago B | North Carolina A | 0 | 0 | 10 | 10 |
| Chicago C | Chicago D | 0 | 0 | 10 | 10 |
| Claremont Colleges | Virginia | 0 | 0 | 10 | 10 |
| Cornell A | Purdue | 0 | 10 | 10 | 20 |
| Cornell B | Vanderbilt | 0 | 0 | 0 | 0 |
| Duke | Florida | 0 | 0 | 10 | 10 |
| Johns Hopkins | Georgia Tech | 0 | 0 | 10 | 10 |
| Harvard | South Carolina | 0 | 10 | 10 | 20 |
| Toronto A | Illinois | 0 | 0 | 10 | 10 |
| Indiana | Columbia A | 0 | 0 | 10 | 10 |
| Kentucky | Minnesota B | 0 | 0 | 10 | 10 |
| Berkeley A | Maryland | 0 | 0 | 10 | 10 |
| Berkeley B | McGill | 0 | 10 | 10 | 20 |
| NYU | Iowa State | 0 | 0 | 0 | 0 |
| North Carolina B | Truman State | 0 | 0 | 10 | 10 |
| Northwestern | Yale A | 0 | 10 | 10 | 20 |
| Ottawa | Toronto B | 0 | 0 | 10 | 10 |
| Stanford | Chicago A | 0 | 10 | 10 | 20 |
| Texas | WUSTL A | 0 | 0 | 10 | 10 |
| Penn | WUSTL B | 0 | 0 | 10 | 10 |
| Waterloo | Minnesota A | 0 | 0 | 10 | 10 |
| Columbia B | Yale B | 0 | 0 | 10 | 10 |