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 ester or unstabilized alkyl reagents. Maryanoff and Reitz coined the term “stereochemical drift” to describe the interconversion of betaine intermediates in this reaction, which can be controlled using the Schlosser modification. (10[2])A modification of this reaction that uses carbanion reagents to preferentially synthesize E products was proposed (10[1])by Leopold Horner. In lithium-free conditions, this reaction proceeds via a four-atom oxaphosphetane intermediate. For 10 points, name this reaction that uses a triphenyl phosphonium (10[1])ylide (“ILL-id”) reagent to convert a carbonyl group into an alkene. ■END■ (10[3]0[7])

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

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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
Arya KarthikOxford ACambridge D6110
Adsayan GaneshWarwick ANYU C6110
Justin LeeImperial ACambridge A7710
Eugenia TongImperial BBristol10210
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