Packet G: Bonus 2
Like the related Buchwald–Hartwig amination, this reaction often uses metal catalysts containing two diphenylphosphine ligands connected via a ferrocene molecule. For 10 points each:
[10m] Name this carbon-carbon bond forming reaction between an organohalide and an aryl or alkyl boronic acid. This reaction’s namesake discoverer shared the Nobel Prize with Richard Heck and Ei-ichi Negishi.
ANSWER: Suzuki reaction [accept Suzuki cross-coupling; or Suzuki–Miyaura cross-coupling or SM cross-coupling or SMC; prompt on cross-coupling reactions or coupling reactions; prompt on palladium-catalyzed reactions or nickel-catalyzed reactions; prompt on organometallic reactions]
[10e] C–C bond formation occurs during the reductive form of this reaction, the last step of the Suzuki catalytic cycle. The E2 type of this reaction outcompetes substitution using bulky bases on secondary alkyl halides.
ANSWER: elimination [accept reductive elimination]
[10h] Ligands with a large value for quantity like diphenylphosphines tend to favor reductive instead of beta-hydride elimination. This quantity does not directly factor in a ligand’s steric bulk, unlike a related quantity introduced by Chadwick Tolman.
ANSWER: bite angle [or omega; prompt on angle; reject “cone angle” or “theta”]
<Rutgers A, Chemistry> | Packet G - McMaster A, Notre Dame C, Rutgers A, NYU A
| Heard | PPB | E % | M % | H % |
|---|---|---|---|---|
| 79 | 11.52 | 77% | 33% | 5% |
Conversion
| Team | Opponent | Part 1 | Part 2 | Part 3 | Total | Parts |
|---|---|---|---|---|---|---|
| Berkeley A | Berkeley C | 10 | 10 | 0 | 20 | ME |
| Berkeley B | Stanford A | 10 | 10 | 0 | 20 | ME |
| Stanford B | Berkeley D | 10 | 10 | 0 | 20 | ME |
Summary
| Tournament | Edition | Match | Heard | PPB | E % | M % | H % |
|---|---|---|---|---|---|---|---|
| California (North) | Main Site | ✓ | 3 | 20.00 | 100% | 100% | 0% |
| California (South) | Main Site | ✓ | 4 | 12.50 | 75% | 50% | 0% |
| Canada | Main Site | ✓ | 11 | 10.00 | 73% | 27% | 0% |
| Florida | Main Site | ✓ | 3 | 6.67 | 67% | 0% | 0% |
| Great Lakes | Main Site | ✓ | 5 | 12.00 | 100% | 20% | 0% |
| Lower Mid-Atlantic | Main Site | ✓ | 9 | 10.00 | 78% | 22% | 0% |
| Midwest | Main Site | ✓ | 8 | 12.50 | 88% | 13% | 25% |
| Northeast | Main Site | ✓ | 6 | 11.67 | 50% | 50% | 17% |
| Overflow | Main Site | ✓ | 4 | 12.50 | 75% | 50% | 0% |
| South Central | Main Site | ✓ | 2 | 10.00 | 100% | 0% | 0% |
| Southeast | Main Site | ✓ | 8 | 11.25 | 75% | 38% | 0% |
| UK | Main Site | ✓ | 12 | 10.00 | 67% | 33% | 0% |
| Upstate NY | Main Site | ✓ | 4 | 17.50 | 100% | 50% | 25% |