Packet 5: Bonus 7
In one version of the Paal-Knorr Synthesis, 1,4-diketones can be reacted with this functional group to form pyrroles. For 10 points each:
[10e] Name this functional group characterized by a carbon-nitrogen single bond.
ANSWER: amines
[10h] In a different reaction developed by Knorr, substituted pyrroles are produced from aminoketones derived from one of these compounds via the Neber rearrangement. A cyclic one of these compounds can undergo a Beckmann rearrangement to form lactams.
ANSWER: oximes [accept ketoximes; prompt on imines]
[10m] Knorr’s pyrrole synthesis begins by forming an imine that undergoes this process, which Knorr discovered in ethyl aceto·acetate. Migration of a hydrogen causes the characteristic interconversion seen in this phenomenon.
ANSWER: tautomerization [or tautomerism]
<MS, Chemistry> | NAFTA-Packet-5
| Heard | PPB | E % | M % | H % |
|---|---|---|---|---|
| 43 | 12.09 | 79% | 33% | 9% |
Conversion
| Team | Opponent | Part 1 | Part 2 | Part 3 | Total | Parts |
|---|---|---|---|---|---|---|
| Berkeley A | Berkeley B | 10 | 0 | 10 | 20 | EM |
| Constans Constantius and Constantine Jr. | Not Old! (Old) | 10 | 10 | 0 | 20 | EH |
| Stanford A | Stanford B | 0 | 0 | 0 | 0 | |
| Team 8 | Team 7 | 10 | 0 | 0 | 10 | E |
Summary
| Tournament | Edition | Match | Heard | PPB | E % | M % | H % |
|---|---|---|---|---|---|---|---|
| 2026 NAFTA at Stanford | 01/17/2026 | ✓ | 4 | 12.50 | 75% | 25% | 25% |
| 2026 NAFTA at UBC | 01/17/2026 | ✓ | 2 | 10.00 | 100% | 0% | 0% |
| 2025 NAFTA Online | 02/14/2026 | ✓ | 4 | 5.00 | 50% | 0% | 0% |
| 2026 NAFTA at Vanderbilt | 02/14/2026 | ✓ | 3 | 16.67 | 100% | 67% | 0% |
| 2025 NAFTA at Toronto | 09/13/2025 | ✓ | 5 | 12.00 | 100% | 20% | 0% |
| 2025 NAFTA at Maryland | 09/27/2025 | ✓ | 5 | 12.00 | 80% | 20% | 20% |
| 2025 NAFTA at Harvard | 10/04/2025 | ✓ | 3 | 10.00 | 67% | 33% | 0% |
| 2025 NAFTA at Oxford | 10/11/2025 | ✓ | 4 | 15.00 | 75% | 75% | 0% |
| 2025 NAFTA at Chicago | 11/08/2025 | ✓ | 6 | 15.00 | 83% | 50% | 17% |
| 2025 NAFTA at Columbia | 11/08/2025 | ✓ | 5 | 14.00 | 80% | 40% | 20% |
| 2025 NAFTA at Richmond | 12/20/2025 | ✓ | 2 | 5.00 | 50% | 0% | 0% |