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 (10[1])“stereochemical drift” (10[2])to describe the interconversion of betaine intermediates in this reaction, which can be controlled (10[1])using the Schlosser modification. A modification of this reaction that uses carbanion reagents to preferentially synthesize E products was proposed 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 ylide (“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>
= Average correct buzz position

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Buzzes

PlayerTeamOpponentBuzz PositionValue
Adam FineChicago AMissouri4110
Akshar GoyalIllinois AWashU A4310
Yash MandaviaIllinois BWashU B4310
Alex AkridgeIndiana AChicago C5710
Ezra SantosChicago BMissoui S&T10410
Benny FeldmanChicago DIndiana B1130
Trenton BurgessIndiana BChicago D1130

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