Question

This reaction occurs twice between a cuprate and an 8-membered enone ring in a total synthesis that starts with serine, whose namesake also modified this reaction. This reaction is the most common mechanism by which acrolein reacts with thiol groups on amino acids. An asymmetric example of this reaction attacks with 4-hydroxycoumarin to synthesize the anticoagulant Warfarin. Both the carbanion (-5[1])“donor” and the alkene (*) “acceptor” of this reaction are stabilized by resonance and contain one or more electron withdrawing groups. (10[1])It’s not the aldol reaction, but a titanium tetrachloride catalyst is used with a silyl enol ether in this reaction’s Mukaiyama (10[1])variant. This reaction has a similar mechanism (10[1])to the Stork enamine (10[1])reaction. This reaction (10[1])begins the Robinson annulation. (10[3]-5[1])For 10 points, (10[1])an enolate is joined to an alpha,beta-unsaturated carbonyl (-5[1])by what 1,4-addition (10[1])reaction? ■END■ (10[4]0[2])

ANSWER: Michael addition [or Michael reaction; prompt on nucleophilic conjugate addition until read; prompt on 1,4-addition or addition until read] (The first clue refers to the Mukaiyama Taxol total synthesis.)
<KP, Chemistry>
= Average correct buzz position

Summary

2024 Chicago Open07/28/2024Y1593%0%20%118.14

Buzzes

PlayerTeamOpponentBuzz PositionValue
Kevin WanggenAI this, genAI that, have you found your 真爱 yetThe Jeam Team59-5
Arya KarthikCharlotte's Moderately Successful TeamLying on a Mattress at Lou’s Apartment in Pilsen, Chicago7910
Eric MukherjeeLMM's LLM MLMPunished "Venom" BHSU10010
Billy BusseBHSU BThe Empire Bikes Back10710
Michael HundingSAYYID QUTB, DRIVING THE LONGEST CAR YOU’VE EVER SEEN THROUGH TAHRIR SQUARENJTRANSit (and anwen, I guess)11110
Adam Finesticking out your guyot for the ridge push; you're so seafloor spread, you're so fracture zoneI’ll take a quiet 10 / A handshake of CO (Chicago Open)11410
Iain CarpenterAre You There, Chat? It's Me, MargaretThere are buzzable clues everywhere for those with eyes to see118-5
Richard NiuAMOGH QUIZ HACK? 英雄联盟 400 PPG 24 TUHRead slowly: A A A A A A A A A A A A A A A Read quickly: A11810
Caleb KendrickWe Need New NamesThe Dyatlov Passement incident11810
Vincent DuA Nervy Liberal Nanny Henceit's the great pumpkinification objection, charlie brown11810
Kevin YeBerkeley Mafia and the Chicago BoyLes Missourables12110
Ryan Westbrookwhen you look this good, you don’t have to know anythingFirst Cause, First Cause, make me young!129-5
Ethan AshbrookGalvanized Square Steen and Eco-Friendly Wood VermeerNJTRANSit (and bobby, i guess)13210
Daniel MaThere are buzzable clues everywhere for those with eyes to seeAre You There, Chat? It's Me, Margaret13410
Mike CheyneThe Oldest Men in the WorldLisan al-Quib13410
Rohan Khervar merchantsMindgoblin of Little Hobbes1340
Jason HongThe Jeam TeamgenAI this, genAI that, have you found your 真爱 yet13410
Walter ZhangMindgoblin of Little Hobbesvar merchants13410
Aidan MehiganFirst Cause, First Cause, make me young!when you look this good, you don’t have to know anything1340