Question
Answer the following about Robert Woodward’s contributions to total syntheses, for 10 points each.
[10e] Woodward led the Harvard team, which joined forces with Albert Eschenmoser’s ETH team, in the total synthesis of this compound. This largest B vitamin’s central corrin ring contains a cobalt atom.
ANSWER: vitamin B12 [or cobalamin]
[10m] The first step of Woodward’s classic strychnine (“STRICK-neen”) synthesis begins with a Fischer indole synthesis, involving a phenyl derivative of this compound. The Olin Raschig process produces this compound found in rocket fuels.
ANSWER: hydrazine [or N2H4; accept phenylhydrazine]
[10h] Woodward and Doering’s 1944 total synthesis of quinine stood until this chemist published a stereoselective pathway in 2001. Carbonyls are selectively alkylated in this chemist’s namesake enamine synthesis.
ANSWER: Gilbert Stork [accept Stork enamine synthesis]
<Chemistry>
Summary
| 2024 ACF Winter at Lehigh | 2024-11-16 | Y | 7 | 12.86 | 100% | 29% | 0% |
| 2024 ACF Winter at Northwestern | 2024-11-16 | Y | 9 | 12.22 | 56% | 56% | 11% |
| 2024 ACF Winter at Ohio State | 2024-11-16 | Y | 9 | 6.67 | 22% | 33% | 11% |
| 2024 ACF Winter at Online | 2024-11-16 | Y | 7 | 15.71 | 86% | 71% | 0% |
| 2024 ACF Winter at Central Florida | 2024-11-16 | Y | 4 | 17.50 | 100% | 50% | 25% |
| 2024 ACF Winter at Oxford | 2024-11-16 | Y | 8 | 11.25 | 63% | 50% | 0% |
Data
| Rowan A | Bard A | 10 | 0 | 0 | 10 |
| Columbia B | Johns Hopkins A | 10 | 0 | 0 | 10 |
| Haverford A | Princeton A | 10 | 0 | 0 | 10 |
| Johns Hopkins B | Rutgers A | 10 | 10 | 0 | 20 |
| Penn State A | Columbia A | 10 | 0 | 0 | 10 |
| Penn State B | Rutgers C | 10 | 10 | 0 | 20 |
| Purdue A | Indiana A | 10 | 10 | 0 | 20 |
| UIUC D | Miami | 0 | 10 | 0 | 10 |
| Northwestern A | Notre Dame | 10 | 10 | 0 | 20 |
| SIUE A | Purdue B | 0 | 0 | 0 | 0 |
| Purdue C | WashU C | 0 | 0 | 0 | 0 |
| Indiana B | UChicago D | 0 | 0 | 0 | 0 |
| UIUC A | UChicago C | 10 | 10 | 0 | 20 |
| WashU B | UIUC B | 10 | 10 | 0 | 20 |
| UChicago B | UIUC C | 10 | 0 | 10 | 20 |
| CWRU A (UG) | Ohio State C (DII) | 0 | 10 | 0 | 10 |
| CWRU C (UG) | Kenyon A (UG) | 0 | 0 | 0 | 0 |
| CWRU D (DII) | Kenyon B (DII) | 0 | 0 | 0 | 0 |
| CWRU B (UG) | Michigan C (UG) | 0 | 0 | 0 | 0 |
| Michigan D (DII) | Michigan State C (UG) | 10 | 0 | 0 | 10 |
| Michigan State A | Pitt A | 0 | 10 | 0 | 10 |
| Pitt B (UG) | Michigan State B (UG) | 0 | 0 | 0 | 0 |
| Ohio State A (UG) | Michigan A | 10 | 0 | 10 | 20 |
| Michigan B | Ohio State B (DII) | 0 | 10 | 0 | 10 |
| Missouri | Iowa | 10 | 10 | 0 | 20 |
| Mississippi State | Central Oklahoma | 10 | 10 | 0 | 20 |
| McGill E | Oregon State | 10 | 0 | 0 | 10 |
| Texas C | Colorado College | 0 | 10 | 0 | 10 |
| Vassar A | Texas A | 10 | 10 | 0 | 20 |
| Vassar B | Texas D | 10 | 0 | 0 | 10 |
| WUSTL A | NYU B | 10 | 10 | 0 | 20 |
| Florida Tech A | UF D | 10 | 0 | 0 | 10 |
| UCF A | Florida State University A | 10 | 10 | 0 | 20 |
| UF B | UCF B | 10 | 10 | 10 | 30 |
| UF E | UF F | 10 | 0 | 0 | 10 |
| Penn A | Penn B | 10 | 0 | 0 | 10 |
| Cambridge A | Bristol A | 10 | 10 | 0 | 20 |
| Cambridge B | Imperial A | 0 | 10 | 0 | 10 |
| Cambridge C | Manchester | 0 | 10 | 0 | 10 |
| Southampton A | Cambridge D | 0 | 0 | 0 | 0 |
| Birmingham | Durham | 10 | 0 | 0 | 10 |
| Imperial B | Warwick A | 10 | 0 | 0 | 10 |
| Oxford A | LSE A | 10 | 10 | 0 | 20 |
| Southampton B | Oxford B | 10 | 0 | 0 | 10 |