Question

Derivatives of this compound that unexpectedly form in solid crystals of cinnamic (“sih-NAM-ick”) acid spurred the development of the topochemical postulate. A derivative of this compound is the intermediate destroyed by retro-aldol cleavage in the de Mayo reaction. A dimerization that forms this compound is the simplest reaction that requires a Möbius twist on p orbitals so that there is one suprafacial and one antarafacial component. 1,4-diradicals recombine to form a derivative of this compound in a type II (“two”) Norrish reaction. (10[2])A metal replaces a carbon atom in this compound (10[1]-5[1])in the intermediate of olefin metathesis (“muh-TATH-uh-siss”). Under light, (10[1])but not heat, (-5[1])alkenes like thymine dimerize to form derivatives of this compound (-5[1])in a [2 + 2] (“two plus two”) cycloaddition. (10[2]-5[4])This compound has bond angles of 88 degrees because it puckers into (10[2])a butterfly (10[1])configuration to reduce ring strain. (10[1])For 10 points, (10[1])name this cyclic alkane containing four (10[1])carbons. (10[1])■END■ (10[6])

ANSWER: cyclobutane [prompt on C4H8; reject “butane”; reject “cyclobutadiene”]
<Chemistry>
= Average correct buzz position

Summary

2023 ACF Nationals04/22/2023Y2190%0%33%125.42

Buzzes

PlayerTeamOpponentBuzz PositionValue
Mazin OmerHarvard AMaryland A7910
Andrew HannaVanderbilt ARutgers A7910
Vittal BhatNorth Carolina AIowa State A88-5
Matt SchiavonePurdue AYale B8810
Andrew SalijNorthwestern ABrown A9610
Geoffrey ChenCornell AVirginia A99-5
Geoffrey WuColumbia AUC Berkeley B109-5
Ethan AshbrookMinnesota AHouston A11510
Noah ChenColumbia BIndiana A115-5
Vivek SasseChicago BJohns Hopkins A115-5
Shahar SchwartzUC Berkeley AImperial A115-5
Dan NiCornell BNYU A11510
Tracy MirkinFlorida AToronto A115-5
Daniel MaYale AOhio State A12710
Karan GurazadaTexas AWUSTL B12710
Adam FineChicago APenn A12910
Paul LeeWUSTL ASouth Carolina A13410
Steven LiuMIT AGeorgia Tech A13710
Benjamin WeinerMinnesota BGeorgia Tech B14310
JD KrothIowa State ANorth Carolina A14410
Maximillian NieburJohns Hopkins AChicago B14510
Subhamitra Banerjee RoychoudhuryMichigan AIllinois A14510
Raymond ChenToronto AFlorida A14510
Vinu HariharUC Berkeley BColumbia A14510
Carlos DoebeliImperial AUC Berkeley A14510
Henry CafaroChicago CDuke A14510