Question

In 2012, Byrne and Gilheany affirmed this reaction progresses differently in salt-containing and salt-free conditions, with the latter scenario being susceptible to “stereochemical drift.” In one mechanism, (15[1])this reaction begins with a [2+2] cycloaddition followed by a fragmentation step. One reagent is replaced with a resonance-stabilized ester carbanion in a variant of this reaction partly named for Leopold Horner. In a modification (15[1])to this reaction, the (15[1])use of (*) phenyllithium leads to the preferential formation of (E)-isomers. This reaction’s intermediate exists in an equilibrium between betaine (10[1])(“bay-tah-een”) and oxaphosphetane (“ock-sah-FOSS-fuh-tain”) forms. This is the most popular reaction used to convert a carbonyl into an alkene. A German chemist names, for 10 points, what reaction that makes use of triphenyl phosphonium ylide reagents? ■END■

ANSWER: Wittig reaction [or Wittig olefination; accept Wittig reagent; accept Horner-Wadsworth-Emmons reaction or HWE reaction until “Horner” is read]
<Kane Nguyen, Chemistry>
= Average correct buzz position

Buzzes

PlayerTeamOpponentBuzz PositionValue
Eric MukherjeeIll-Advised Buzzbruh2615
Tracy MirkinStatler and Waldorfesque Former Penn Bowl EditorsKhalil v Carbolic Shisha Ball Co6115
Stephen LiuWe joppingOh you like geography? Name every Forrest.6515
Dan NiTOADWhy the Kremlin Hates Bananas8410

Summary

2024 Penn Bowl Playtest10/12/2024Y4100%75%0%59.00
2024 Penn Bowl UNC10/26/2024N3100%33%33%89.67
2024 Penn Bowl Florida10/26/2024N2100%50%0%92.00
2024 Penn Bowl Harvard10/26/2024N475%25%0%66.33
2024 Penn Bowl UK10/26/2024N580%40%20%87.50
2024 Penn Bowl Berkeley11/02/2024N2100%0%0%79.50
2024 Penn Bowl Mainsite11/02/2024N367%0%33%117.00
2024 Penn Bowl CWRU11/02/2024N425%0%0%119.00
2024 Penn Bowl Chicago11/02/2024N888%38%25%82.14
2024 Penn Bowl Texas11/02/2024N250%0%0%116.00