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

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

PlayerTeamOpponentBuzz PositionValue
Richard NiuCornell BVassar A4210
Noah ChenColumbia BGeorge Washington B4910
Jerry VinokurovJohn Jay CollegePenn A8010
Maximilian NieburJohns Hopkins AColumbia C8010
Frederick Rivas-GiorgiYale AGeorge Washington A9710
Ryan RosenbergNYU AMaryland B10310
Andy YuMaryland AHaverford B10410
Vinayak Singh BhadoriyaNYU BHaverford A1130
Arjun BothraHaverford ANYU B1130

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