Wolff–Kishner reduction - 2025 ACF Winter

Question

This doubly-eponymous reaction can often lead to azide-forming side reactions. For 10 points each:

[10m] Name this reaction that uses hydrazine to perform the reduction of a carbonyl. Unlike the Clemmensen reduction, this reaction requires highly basic conditions.

ANSWER: Wolff–Kishner reduction

[10e] Hydrazine consists of two atoms of this element bonded to four atoms of hydrogen. Hydrazine has a similar odor to ammonia due to them both containing this element.

ANSWER: nitrogen [or N]

[10h] As the Clemmensen and Wolff–Kishner reductions are harsh reactions, this multi-step reaction using dithiols can be used instead. Thioketal intermediates formed in this process can then be converted using Raney nickel.

ANSWER: Mozingo reduction [or Mozingo reaction or thioketal reduction]

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Summary


California	Main	Y	5	12.00	100%	20%	0%
Canada	Main	Y	6	11.67	100%	0%	17%
Florida	Main	Y	13	10.77	92%	15%	0%
Great Lakes	Main	Y	6	11.67	83%	33%	0%
Lower Mid-Atlantic	Main	Y	7	10.00	100%	0%	0%
Midwest	Main	Y	10	12.00	90%	30%	0%
North	Main	Y	11	14.55	100%	46%	0%
Northeast	Main	Y	5	14.00	100%	40%	0%
Overflow	Main	Y	4	12.50	100%	25%	0%
Pacific Northwest	Main	Y	12	11.67	100%	17%	0%
South Central	Main	Y	5	10.00	80%	20%	0%
Southeast	Main	Y	12	14.17	100%	42%	0%
Upper Mid-Atlantic	Main	Y	8	13.75	100%	25%	13%
2025 ACF Nationals	2025-08-09	Y	14	12.14	93%	14%	14%
2024 ARCADIA at UC Berkeley	04/19/2025	Y	4	10.00	100%	0%	0%
UK (South)	UK	N	2	10.00	100%	0%	0%

Data


Stanford A	Berkeley E	0	10	0	10
Berkeley D	Stanford B	10	10	0	20
Berkeley A	Berkeley C	0	10	0	10
Stanford C	Berkeley F	0	10	0	10
Claremont Pitzer	UCI	0	10	0	10
UCLA A	UCLA C	0	10	10	20
UCLA B	UCLA D	0	10	0	10
UCSB	UCSD Two Running Violet V Forms	0	10	0	10
UCSD Vices and Virtues	USC	0	10	0	10
Claremont Scripps	UCSD What Hath God Wrought	0	10	0	10
Berkeley B	UCSC	0	10	0	10
Carleton	McGill C	0	10	0	10
McGill A	Ottawa	0	10	0	10
Queen's A	McGill B	0	10	0	10
McMaster B	Waterloo	0	10	0	10
Queen's B	Toronto E	0	10	0	10
Toronto A	McMaster A	10	10	0	20
Toronto B	Toronto C	10	10	0	20
Toronto G	Toronto F	0	10	0	10
Toronto I	Toronto H	0	10	0	10
Toronto J	Toronto Metropolitan	0	10	0	10
Toronto K	McMaster C	0	10	0	10
Western Ontario	Guelph B	0	0	0	0
Guelph A	Toronto D	0	10	0	10
FIU	ERAU A	0	10	0	10
ERAU B	UF D	0	0	0	0
UCF A	FSU	10	10	0	20
UCF B	Melbourne A	0	10	0	10
UF C	UF A	10	10	0	20
UF E	UF B	0	10	0	10
CWRU A	OSU C	0	10	0	10
CWRU B	Pitt A	0	10	0	10
CWRU D	MSU B	0	10	0	10
Kenyon A	Pitt C	0	10	0	10
CWRU C	MSU A	0	10	0	10
OSU D	Kenyon B	0	10	0	10
Pitt B	OSU A	0	10	0	10
Virginia Tech A	James Madison	0	10	0	10
Liberty C	Virginia B	0	0	0	0
North Carolina B	Tennessee B	10	10	0	20
North Carolina C	Roanoke	0	10	0	10
South Carolina A	South Carolina B	10	10	0	20
Tennessee A	Liberty B	10	10	0	20
NC State	Tusculum	0	10	0	10
Virginia A	North Carolina A	0	10	0	10
Clemson B	Virginia Tech B	0	10	0	10
Maryland A	Penn A	10	10	0	20
Maryland B	Penn B	10	10	0	20
Johns Hopkins A	Maryland C	0	10	0	10
NYU A	George Mason B	10	10	0	20
George Mason A	NYU B	10	10	0	20
Notre Dame E	Georgetown B	0	10	0	10
Georgetown A	VCU A	0	10	0	10
Catholic University	Maryland D	0	10	0	10
UMBC A	George Washington A	0	10	0	10
Johns Hopkins C	George Washington B	0	10	0	10
Johns Hopkins B	George Mason C	10	10	0	20
Liberty A	Clemson A	0	10	0	10
Columbia B	Lehigh B	10	10	0	20
Lehigh A	Columbia C	0	10	0	10
Princeton A	Rutgers C	0	10	0	10
Swarthmore A	Rutgers B	0	10	0	10
Columbia A	Vassar A	10	10	0	20
SIUE	WashU B	0	10	0	10
Truman State	William Woods	0	10	0	10
Missouri A	WashU A	10	10	0	20
WashU C	WashU D	0	10	0	10
Chicago B	Chicago A	10	10	0	20
Notre Dame A	Chicago C	0	10	0	10
Chicago D	Louisville B	0	10	0	10
Illinois A	Illinois C	0	10	0	10
Michigan A	Indiana A	0	10	0	10
Illinois B	Michigan C	10	10	0	20
Michigan D	Purdue C	0	10	0	10
Louisville A	Notre Dame B	0	10	0	10
Indiana B	Notre Dame D	0	10	0	10
Michigan B	Purdue A	0	10	0	10
Notre Dame C	Purdue B	0	10	0	10
Kentucky	UIC	0	10	0	10
Macalester A	Carleton	0	0	0	0
Iowa State	Minnesota C	0	10	0	10
Nebraska	Minnesota B	0	10	0	10
Minnesota A	Wisconsin	10	10	0	20
Macalester B	St. Thomas	0	10	0	10
Brown A	Amherst B	0	10	0	10
Brandeis Clemenceau	BC A	0	10	0	10
BC B	Bowdoin A	0	10	0	10
BU	Bowdoin B	10	10	0	20
Amherst A	Brandeis Lloyd George	0	10	0	10
Brown B	Brandeis Orlando	0	10	0	10
Harvard	Dartmouth	10	10	0	20
MIT A	Cornell-UG	10	10	0	20
MIT B	Brandeis Wilson	0	10	0	10
Yale A	Tufts A	10	10	0	20
Tufts B	Yale B	10	10	0	20
Brown C	Williams	0	10	0	10
Ohio	Alberta B	0	10	0	10
Texas A	Rose State	0	10	0	10
Texas B	Arizona State A	0	10	0	10
Tulsa	Northwestern C	0	10	0	10
UCO	Arizona State B	10	10	0	20
UTD A	Northwestern B	0	10	0	10
Iowa	UTD B	0	10	0	10
Northwestern A	McGill D	10	10	10	30
Edinburgh A	Bristol B	0	10	0	10
Cambridge A	LSE B	0	10	10	20
Cambridge C	Imperial B	10	10	10	30
Durham A	Cambridge D	0	10	0	10
City St George's A	Birmingham A	0	0	0	0
Edinburgh B	Bristol A	0	10	0	10
Southampton A	Imperial C	0	10	0	10
LSE A	Lancaster A	0	10	0	10
Manchester A	Sheffield C	0	10	0	10
Manchester B	Warwick B	0	10	0	10
Oxford A	Durham B	10	10	0	20
Sheffield A	Oxford B	0	10	0	10
Sheffield B	Cambridge B	0	10	0	10
Warwick A	Southampton B	0	10	0	10
ESF	Rochester	0	10	0	10
Cornell-DII	Binghamton A	0	10	0	10
Syracuse	Binghamton B	0	10	0	10
RIT A	RIT B	0	10	0	10