Question

Bruce Lipshutz used Merrifield resin to scavenge this molecule and its tricky-to-separate oxidized derivative after reactions using Ni(0) (“nickel-zero”). Adding an acyl group to this molecule, rather than an ester, allows it to be cleaved during a reaction’s “traceless” variant. Four copies (-5[1])of this molecule are ligands on a tetrahedral complex that supplies palladium to cross-couplings. (10[1])An excess (-5[1])of this molecule is separated alongside waste hydrazines in a reaction in which it prepares an alcohol for (10[1])SN2 substitution after attacking the azo group of DIAD (“D-I-A-D”). This molecule is the (10[1])bulkiest ligand on Wilkinson’s catalyst. (10[5])This molecule lies (10[1])at one corner (-5[1])of the square intermediate formed (10[1])by a carbonyl and an ylide (10[1])(“ILL-id”). This molecule is a key reagent in both the Mitsunobu and Wittig reactions. For 10 points, name this bulky compound with three aryl (10[1])groups (10[1])bound to phosphorus. (10[1]0[1])■END■ (10[4]0[2])

ANSWER: triphenylphosphine (“tri-phenyl-phosphine”) [accept Ph3PO, triphenylphosphine oxide, triphenylphosphonium ylide, or tetrakis(triphenylphosphine) palladium(0); prompt on TPPO by asking “what does that stand for?”]
<Chemistry>
= Average correct buzz position

Summary

2024 ACF Nationals2024-04-21Y2090%0%15%107.28

Buzzes

PlayerTeamOpponentBuzz PositionValue
Andrew WangIllinoisOttawa40-5
Nikhil ChellamNorthwesternStanford5410
Sinecio MoralesJohns HopkinsNYU56-5
Justin ZhangDukeMinnesota B7410
Richard NiuCornell AToronto B8710
Ethan AshbrookMinnesota AChicago C9210
Geoffrey WuColumbia AClaremont Colleges9210
Jason HongBrownMcGill9210
Matt SchiavonePurdueTruman State9210
Adam FineChicago ASouth Carolina9210
Neal JoshiWUSTL BYale A9510
Andrew EllisKentuckyToronto A98-5
Shahar SchwartzBerkeley ANorth Carolina B10310
Andrew HannaPennMaryland10910
Aidan FeinVanderbiltYale B13210
Kushal AluruRutgersHarvard13310
Adrian WongOttawaIllinois1360
Raymond ChenToronto AKentucky13610
Ryan HumphreyTexasCornell B13710
Alex AkridgeIndianaFlorida13710
Derek ChenColumbia BMichigan13710
Eshan PantNYUJohns Hopkins1370
Kenny ZhangVirginiaNorth Carolina A1370
Vincent DuNorth Carolina AVirginia13710