Bonus

This side product and a carbocation can be produced following the protonation of a di·azo group. For 10 points each:
[10m] Name this extremely stable leaving group whose removal acts as the thermodynamically restrictive final step of the Wolff–Kishner reduction.
ANSWER: dinitrogen gas [accept N2]
[10h] In the Cram modification of the Wolff–Kishner reduction, one of these functional groups is added directly instead of being formed as an intermediate. A tosylated version of this group is the leading group in the Shapiro and Bamford–Stevens reactions.
ANSWER: hydrazones [accept tosylhydrazone; reject “hydrazine”]
[10e] Instead of being kicked off as leaving groups, two connected nitrogen groups can be converted into azo groups in many syntheses for these substances. Other nitrogenous compounds used for this purpose include mauve and indigo.
ANSWER: dyes [accept pigments; accept colored molecules]
<Chemistry>
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Conversion

TeamOpponentPart 1Part 2Part 3TotalParts
British ColumbiaArizona State1001020ME
Chicago AIndiana10101030MHE
Chicago BVirginia Tech001010E
Columbia AToronto A10101030MHE
Columbia BOhio State001010E
FloridaWUSTL B001010E
Georgia StatePenn State001010E
Georgia TechToronto B001010E
Illinois AWaterloo A1001020ME
Iowa StateHarvard001010E
LSEYale001010E
MITMinnesota1001020ME
MarylandRIT001010E
MichiganIllinois B1001020ME
OttawaNYU001010E
RutgersNorthwestern001010E
StanfordUC Berkeley A1001020ME
TexasJohns Hopkins001010E
Toronto CCornell A001010E
UCFVirginia001010E
VanderbiltCornell B0000
WUSTL ANorth Carolina A001010E
Waterloo BUC Berkeley B0101020HE
Winona StateNorth Carolina B001010E

Summary

TournamentExact Match?HeardPPBEasy %Medium %Hard %
2025 ACF NationalsYes2413.7596%29%13%