Question
One of these ions called armilenium was proposed to be the first entirely organic sandwich compound, but it was found to be fluxional, with the sandwich structure not even an intermediate between its twenty stable configurations. For 10 points each:
[10e] Name these ions whose stable examples include trityl, or triphenylmethyl. These ions feature a carbon atom with a positive charge.
ANSWER: carbocations [or carbonium; or carbenium]
[10m] Hyperconjugation ensures that tertiary carbocations are particularly stable, including this simplest tertiary carbocation.
ANSWER: tert-butyl cation [or t-butyl cation; or t-Bu+; prompt on butyl cation; reject “n-butyl”, “sec-butyl”, or “isobutyl”]
[10h] This carbocation derived from a bridged hydrocarbon was the subject of a lengthy dispute over its structure, with it being confirmed to be non-classical rather than rapidly equilibrating between two classical structures.
ANSWER: 2-norbornyl cation [or 2-bicyclo[2.2.1]heptyl cation; reject “1-norbornyl” or “7-norbornyl”]
<Gerhardt Hinkle, Chemistry>
Summary
| 2023 Penn Bowl @ Waterloo | 10/28/2023 | Y | 4 | 10.00 | 100% | 0% | 0% |
| 2023 Penn Bowl @ FSU | 10/28/2023 | Y | 2 | 0.00 | 0% | 0% | 0% |
| 2023 Penn Bowl (Harvard) | 10/21/2023 | Y | 3 | 10.00 | 67% | 33% | 0% |
| 2023 Penn Bowl (Mainsite) | 10/21/2023 | Y | 7 | 8.57 | 71% | 0% | 14% |
| 2023 Penn Bowl (South Central) | 10/28/2023 | Y | 3 | 6.67 | 67% | 0% | 0% |
| 2023 Penn Bowl (UK) | 10/28/2023 | Y | 5 | 14.00 | 100% | 20% | 20% |
| 2023 Penn Bowl @ UNC | 10/28/2023 | Y | 3 | 16.67 | 100% | 33% | 33% |