Packet E: Bonus 13
This functional group can be added to arenes (“AIR-eens”) using the Vilsmeier–Haack reagent, which is formed in situ from phosphorus oxychloride and DMF. For 10 points each:
[10h] Name this functional group added to phenols using chloroform and a strong base in the Reimer–Tiemann reaction. An industrial process for adding this functional group to alkenes uses rhodium complexed to sodium salts of sulfonated triphenylphosphine.
ANSWER: formyl group [accept formylation or hydroformylation; accept aldehyde; accept CHO or COH; prompt on carbonyl or CO] (The industrial process is the Ruhrchemie/Rhone–Poulenc process, and the ligand is TPPTS.)
[10m] Deprotonating chloroform generates these compounds for EAS (“E-A-S”) in the Reimer–Tiemann reaction. Lone pairs of the N-heterocyclic type of these compounds coordinate ruthenium in Grubbs catalysts used for olefin metathesis.
ANSWER: carbenes [accept N-heterocyclic carbenes or NHCs; accept persistent carbenes; accept dichlorocarbenes]
[10e] The Reimer–Tiemann reaction has largely supplanted Gattermann–Koch formylation for the production of salicylaldehyde (“SAL-uh-sill-aldehyde”) due to the latter’s use of this toxic gas that competes with O2 for binding to hemoglobin.
ANSWER: carbon monoxide [or CO]
<AL, Chemistry> | Packet E - Chicago A, Toronto B, Brandeis B, JHU A
| Heard | PPB | E % | M % | H % |
|---|---|---|---|---|
| 75 | 10.13 | 91% | 7% | 4% |
Conversion
| Team | Opponent | Part 1 | Part 2 | Part 3 | Total | Parts |
|---|---|---|---|---|---|---|
| Catholic | Johns Hopkins B | 0 | 0 | 10 | 10 | E |
| Columbia A | Maryland C | 10 | 0 | 10 | 20 | HE |
| Columbia B | Maryland B | 0 | 10 | 10 | 20 | ME |
| John Jay | NYU C | 0 | 0 | 10 | 10 | E |
| Maryland A | Rutgers A | 0 | 0 | 10 | 10 | E |
| NYU B | Vassar | 0 | 0 | 10 | 10 | E |
| Rutgers B | Georgetown | 0 | 0 | 10 | 10 | E |
| Swarthmore | Columbia C | 0 | 0 | 10 | 10 | E |
Summary
| Tournament | Edition | Match | Heard | PPB | E % | M % | H % |
|---|---|---|---|---|---|---|---|
| California (North) | Main Site | ✓ | 3 | 6.67 | 67% | 0% | 0% |
| California (South) | Main Site | ✓ | 4 | 10.00 | 75% | 25% | 0% |
| Canada | Main Site | ✓ | 1 | 10.00 | 100% | 0% | 0% |
| Florida | Main Site | ✓ | 3 | 10.00 | 100% | 0% | 0% |
| Great Lakes | Main Site | ✓ | 5 | 10.00 | 100% | 0% | 0% |
| Lower Mid-Atlantic | Main Site | ✓ | 9 | 8.89 | 89% | 0% | 0% |
| Midwest | Main Site | ✓ | 8 | 11.25 | 100% | 13% | 0% |
| Northeast | Main Site | ✓ | 5 | 10.00 | 60% | 0% | 40% |
| Overflow | Main Site | ✓ | 4 | 10.00 | 100% | 0% | 0% |
| South Central | Main Site | ✓ | 2 | 10.00 | 100% | 0% | 0% |
| Southeast | Main Site | ✓ | 7 | 8.57 | 86% | 0% | 0% |
| UK | Main Site | ✓ | 12 | 10.83 | 92% | 17% | 0% |
| Upper Mid-Atlantic | Main Site | ✓ | 8 | 12.50 | 100% | 13% | 13% |
| Upstate NY | Main Site | ✓ | 4 | 10.00 | 100% | 0% | 0% |