Question

This reaction is the basis for a modification that uses electron-deficient reagents in a mixture of KHMDS and 18-crown-6. Semi-stabilized aryl reagents in this reaction do not achieve stereoselectivity, unlike stabilized (10[1])ester or unstabilized (10[1])alkyl reagents. Maryanoff and Reitz coined the term (10[1])“stereochemical (10[1])drift” (10[2])to describe the interconversion of betaine (10[1])intermediates in this reaction, (10[2])which can be controlled (10[1])using the Schlosser modification. (10[4])A modification of this reaction that uses carbanion reagents (10[1])to preferentially synthesize E products was proposed (10[1])by Leopold Horner. (10[2])In lithium-free (10[1])conditions, this reaction proceeds via a four-atom (10[1])oxaphosphetane intermediate. For 10 points, (10[1])name this reaction (10[1])that uses a triphenyl (10[2])phosphonium (10[6])ylide (10[2])(“ILL-id”) reagent (10[3])to convert (10[2])a carbonyl group into an alkene. ■END■ (10[4]0[25])

ANSWER: Wittig (“VIT-ig”) reaction [or Wittig olefination; prompt on Horner–Wadsworth–Emmons reaction until “Horner” is read]
<UBC, Chemistry>
= Average correct buzz position

Summary

California2025-02-01Y3100%0%0%88.33
Florida2025-02-01Y250%0%0%102.00
Great Lakes2025-02-01Y560%0%0%102.67
Midwest2025-02-01Y683%0%0%57.60
North2025-02-01Y367%0%0%104.00
Northeast2025-02-01Y560%0%0%49.00
Overflow2025-02-01Y4100%0%0%73.25
South Central2025-02-01Y2100%0%0%67.50
Southeast2025-02-01Y450%0%0%101.50
UK2025-02-01Y1070%0%0%91.43
Upper Mid-Atlantic2025-02-01Y888%0%0%79.29
Upstate NY2025-02-01Y367%0%0%104.50

Buzzes

PlayerTeamOpponentBuzz PositionValue
Matt SchiavoneNorthwestern AGeorgetown A3010
Max NealHarvard BBU3310
Adam FineChicago AMissouri4110
Richard NiuCornell BVassar A4210
Akshar GoyalIllinois AWashU A4310
Yash MandaviaIllinois BWashU B4310
Noah ChenColumbia BGeorge Washington B4910
Arjun NageswaranHarvard ATufts A5310
Viraj NegandhiTexas BTAMU5310
Alex AkridgeIndiana AChicago C5710
Rohan ShelkeUC Berkeley BClaremont B6110
Mason YuBrown AMIT A6110
Arya KarthikOxford ACambridge D6110
Adsayan GaneshWarwick ANYU C6110
Stan MelkumianPurdueNotre Dame C7010
Justin LeeImperial ACambridge A7710
Jerry VinokurovJohn Jay CollegePenn A8010
Maximilian NieburJohns Hopkins AColumbia C8010
Bryan UgazASUTexas A8210
Allan LeeStanford BNorthwestern B8910
Calvin BostlemanOhio State AMichigan C9410
Frederick Rivas-GiorgiYale AGeorge Washington A9710
Enina EdosomwanCase Western AOhio State B10110
Rohan DalalGeorgia Tech CTennessee A10110
Swapnil GargUC Berkeley AUCLA10210
Kevin ParkClaremont AUCSD10210
Bill ZhaoFlorida BValencia A10210
Drew WetterlindIowa StateWinona State10210
Jack LewisBruin AGeorgia Tech A10210
Eugenia TongImperial BBristol10210
Ryan RosenbergNYU AMaryland B10310
Cade ReinbergerRIT ACornell C10310
Ezra SantosChicago BMissoui S&T10410
Jacob FinleyNotre Dame AIowa10410
Andy YuMaryland AHaverford B10410
Foster HughesMinnesota BWisconsin B10610
Pranaav SenthilkumarCornell DESF A10610
Tiffany ZhouFlorida AFlorida State A1130
Cade SmithMichigan StateCarnegie Mellon A1130
Biyang ZhangMichigan BKenyon1130
Yashwanth BajjiMichigan AMichigan D11310
David NiemanCarnegie Mellon AMichigan State1130
Benny FeldmanChicago DIndiana B1130
Trenton BurgessIndiana BChicago D1130
Nithin MenduWisconsin ACarleton1130
Aaron MarchandCarletonWisconsin A1130
Elliott GomesDartmouth AUMass Boston1130
Nathaniel MartinBrandeis ABrandeis B1130
Harris BecknerAlabama AGeorgia Tech B1130
Brina RatangeeVanderbilt AGeorgia Tech D1130
Monish JampalaGeorgia Tech DVanderbilt A1130
Matthew SumanenGeorgia Tech BAlabama A1130
Benjamin WatsonOxford CCambridge B1130
Lewis StrachanCambridge ESouthampton B1130
Joel DickerSouthampton BCambridge E11310
Shiv SeshanCambridge BOxford C1130
Roselyn DaffinSouthampton ALSE1130
Andy HuffLSESouthampton A1130
Alex BakerCambridge COxford B11310
Tobin PayneWarwick BSheffield11310
Hamish CampbellDurhamManchester1130
Joel CrossleyManchesterDurham1130
Vinayak Singh BhadoriyaNYU BHaverford A1130
Arjun BothraHaverford ANYU B1130
Emilie MooreRIT BBinghamton A1130
Elijah O’Sick JohnsonBinghamton ARIT B1130