Question
This compound’s heptanitro- derivative may be a more potent explosive than octogen. For 10 points each:
[10h] Name this compound first synthesized in 1964 by Philip Eaton and Thomas Cole, whose structure was once thought to be impossible. This compound’s highly-strained sp3 carbons make it useful for energy-storage purposes.
ANSWER: cubane
[10e] Cubane has been investigated as a bioisostere for this compound in drugs like lumacaftor, since cubane groups are often more soluble and don’t get oxidized by cytochromes p450. This aromatic hydrocarbon has formula C6H6.
ANSWER: benzene
[10m] Two answers required. Part of the difficulty with using cubane as a benzene bioisostere is that it’s very hard to synthesize 1,3 (“one-three”) and 1,2- (“one-two”) disubstituted cubanes, which correspond to substitutions at these two positions. These two substitution positions are closest to the original substituent.
ANSWER: ortho AND meta [or O AND M]
<JF, Chemistry>
Summary
| 2024 ARCADIA at Waterloo | 2024-11-09 | Y | 6 | 13.33 | 100% | 33% | 0% |
| 2024 ARCADIA at Illinois | 2024-11-09 | Y | 4 | 15.00 | 100% | 0% | 50% |
| 2024 ARCADIA at Claremont | 2024-11-02 | Y | 3 | 13.33 | 100% | 33% | 0% |
Data
| Chicago A | SIUE | 10 | 10 | 0 | 20 |
| Illinois Orange | Chicago B | 0 | 10 | 0 | 10 |
| Purdue B | Notre Dame | 0 | 10 | 0 | 10 |
| Illinois Blue | Purdue A | 10 | 10 | 0 | 20 |