category: gpqa

answer: C

pred: C


answer: C

pred: B


answer: A

pred: A


answer: B


answer: C


answer: D

pred: D


answer: C


answer: A


answer: A


answer: B


answer: D


answer: A


answer: D

pred: Scenario: Starting with exocyclic double bond CH2=C(CH3)- attached to ring at carbon Cβ (the sp2 carbon). After peracid epoxidation, you get an epoxide ring connecting CH2 (Cα) and Cβ. The O is bridging these. The nucleophile (methoxide) attacks the less substituted carbon (Cα, the CH2). It attacks backside to open the epoxide, resulting in CH2-OMe (i.e., CH2OCH3) and O- attached to Cβ. So O- remains attached to Cβ, which


answer: D


answer: D


answer: C


answer: B


answer: A


answer: B


answer: B


answer: B


answer: A


answer: C


answer: B


answer: B

pred: We need to reconsider the possibility that B is 4-methyl-1-phenylpent-3-en-1-one, and the reaction is the "Claisen rearrangement of an allyl vinyl ether"? But that is not a vinyl ether but a ketone.


answer: D


answer: C


answer: C


answer: A


answer: D


answer: D

pred: That product 3 is a symmetric compound with a plane of symmetry only (Cs). Among the answer choices, they include Cs, which is a common point group for many molecules that have one plane of symmetry but no rotational axis. For a condensation product of acetone and an aldehyde, the result often is an α,β-unsaturated carbonyl that has a mirror plane (the molecule is planar), so its point group is Cs.


answer: D


answer: C


answer: D


answer: D


answer: D


answer: C


answer: C


answer: A


answer: B


answer: B


answer: B


answer: D


answer: C


answer: D


answer: B


answer: C


answer: B


answer: C

pred: If we treat it as an allyl vinyl ether: The allyl part is CH2=CH-CH2-? Actually the O is attached to CH2 (the vinyloxy CH2). So the O–CH2 is connecting the vinyl group CH=CH2 (vinyloxy) to the allylic moiety (the but-1-ene). The allyl fragment attached to O comprises CH2 (attached to O)–C2 (sp2 carbon)–C1 (CH2) maybe? Let's see: O–CH2–C2 (sp2)–C1=CH2? That is an allyl fragment indeed: O-CH2-CH=CH2 is allyl vinyl ether; but we have O-CH2-CH (connected to CH2CH3) and double bond at CH2=CH? Wait, the double bond is CH2=CH-CR2


answer: A