Gilbert Stork devoted a controversial footnote of their pioneering quinine synthesis to dismissing quinine’s first formal synthesis, which was conducted by this scientist and Robert Woodward. For 10 points each:
[10h] Name this chemist who determined the mechanism of the Baeyer–Villiger oxidation with Edwin Dorfman. This scientist worked with Wolfgang Roth to identify a reaction’s chair transition state.
ANSWER: William Doering [or William von Eggers Doering; accept Doering–Dorfman experiment or Doering–Roth experiment]
[10m] Doering and Roth predicted that bullvalene (“BULL-vuh-leen”) would only have one proton NMR peak because of how rapidly it undergoes this sigmatropic reaction.
ANSWER: Cope rearrangement [prompt on Cope reaction; prompt on rearrangement; reject “Cope elimination”]
[10e] Bullvalene can undergo this many possible rearrangements at any given moment, as each swaps the bridgehead carbon with a cyclopropyl (“cyclo-PRO-pill”) carbon. There are this many carbons in propane.
ANSWER: three [or 3]
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