Packet J: Bonus 6
This phenomenon can explain why acetolysis rates for exo-substituted 2-norbornanes are 350 times greater than those for endo-substituted isomers. For 10 points each:
[10h] Name this phenomenon where a reaction center interacts with a non-conjugated lone pair or bonding electrons in the same molecule. A classic example of this phenomenon is the elevated SN2 rates for nitrogen mustards.
ANSWER: neighboring group participation [or NGP; accept anchimeric assistance]
[10m] In another example of NGP, pi electrons stabilize the 2-norbornyl one of these species, which George Olah isolated using magic acids. These species migrate to achieve more stable configurations in hydride or methyl shifts.
ANSWER: carbocations [accept carbenium ions; accept carbonium ions; prompt on cations or ions]
[10e] The 2-norbornyl cation can be described non-classically using bonds consisting of two electrons distributed over this many centers. Banana bonds are used to model cyclopropane, which has this many carbon atoms.
ANSWER: three [accept three-center two-electron bonds]
<Edinburgh A, Chemistry> | Packet J - Southampton A, Indiana A, Illinois B, Edinburgh A
| Heard | PPB | E % | M % | H % |
|---|---|---|---|---|
| 80 | 12.00 | 76% | 40% | 4% |
Conversion
| Team | Opponent | Part 1 | Part 2 | Part 3 | Total | Parts |
|---|---|---|---|---|---|---|
| Claremont | Washington B | 0 | 10 | 10 | 20 | ME |
| Minnesota A | Georgia Tech A | 0 | 10 | 10 | 20 | ME |
| Missouri B | Carleton College | 0 | 0 | 0 | 0 |
Summary
| Tournament | Edition | Match | Heard | PPB | E % | M % | H % |
|---|---|---|---|---|---|---|---|
| California (North) | Main Site | ✓ | 3 | 16.67 | 100% | 67% | 0% |
| California (South) | Main Site | ✓ | 4 | 10.00 | 75% | 25% | 0% |
| Canada | Main Site | ✓ | 11 | 14.55 | 91% | 46% | 9% |
| Florida | Main Site | ✓ | 3 | 3.33 | 33% | 0% | 0% |
| Great Lakes | Main Site | ✓ | 5 | 18.00 | 100% | 80% | 0% |
| Lower Mid-Atlantic | Main Site | ✓ | 9 | 8.89 | 56% | 33% | 0% |
| Midwest | Main Site | ✓ | 8 | 13.75 | 88% | 38% | 13% |
| Northeast | Main Site | ✓ | 5 | 16.00 | 100% | 40% | 20% |
| Overflow | Main Site | ✓ | 3 | 13.33 | 67% | 67% | 0% |
| South Central | Main Site | ✓ | 2 | 10.00 | 50% | 50% | 0% |
| Southeast | Main Site | ✓ | 8 | 10.00 | 63% | 38% | 0% |
| UK | Main Site | ✓ | 6 | 10.00 | 67% | 33% | 0% |
| Upper Mid-Atlantic | Main Site | ✓ | 9 | 13.33 | 89% | 44% | 0% |
| Upstate NY | Main Site | ✓ | 4 | 5.00 | 50% | 0% | 0% |