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. 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, (10[1])name this reaction that uses a triphenyl (10[1])phosphonium ylide (“ILL-id”) reagent to convert a carbonyl group into an alkene. ■END■ (10[1]0[3])

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
Calvin BostlemanOhio State AMichigan C9410
Enina EdosomwanCase Western AOhio State B10110
Biyang ZhangMichigan BKenyon1130
Yashwanth BajjiMichigan AMichigan D11310
Cade SmithMichigan StateCarnegie Mellon A1130
David NiemanCarnegie Mellon AMichigan State1130

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