William Doering - 2024 ACF Nationals

Question

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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Data

Team	Opponent	Part 2	Part 3	Total
Berkeley A	Maryland	0	10	10
Berkeley B	McGill	10	10	20
Chicago B	North Carolina A	0	10	10
Chicago C	Chicago D	0	10	10
Claremont Colleges	Virginia	0	10	10
Columbia B	Yale B	0	10	10
Cornell A	Purdue	10	10	20
Cornell B	Vanderbilt	0	0	0
Duke	Florida	0	10	10
Harvard	South Carolina	10	10	20
Indiana	Columbia A	0	10	10
Johns Hopkins	Georgia Tech	0	10	10
Kentucky	Minnesota B	0	10	10
Michigan	Brown	0	10	10
NYU	Iowa State	0	0	0
North Carolina B	Truman State	0	10	10
Northwestern	Yale A	10	10	20
Ottawa	Toronto B	0	10	10
Penn	WUSTL B	0	10	10
Rutgers	Arizona State	10	10	20
Stanford	Chicago A	10	10	20
Texas	WUSTL A	0	10	10
Toronto A	Illinois	0	10	10
Waterloo	Minnesota A	0	10	10

Summary

Tournament	Edition	Exact Match?	Heard	PPB	Easy %	Medium %	Hard %
2024 ACF Nationals	04/21/2024	Y	24	11.67	92%	25%	0%