oxidation - 2025 ACF Regionals

Question

Pyridinium chlorochromate, or PCC, is a reagent that can perform a mild type of this reaction. For 10 points each:

[10e] Name this type of reaction exemplified by the conversion of an alcohol to a carbonyl group, such as in one named for Jones. This type of reaction corresponds to a loss of electrons.

ANSWER: oxidation [accept Jones oxidation]

[10m] This oxidation converts an alcohol to a carbonyl using oxalyl chloride in an “activated DMSO” reaction. The notoriously odorous dimethyl sulfide is produced as a byproduct of this reaction.

ANSWER: Swern oxidation

[10h] The Corey–Kim oxidation uses dimethyl sulfide and a chlorine derivative of this compound. Bromine radicals used for allylic bromination come from a derivative of this compound in the Wohl–Ziegler reaction.

ANSWER: succinimide [or N-chlorosuccinimide or N-bromosuccinimide; prompt on NCS or NBS]

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Summary


California	2025-02-01	Y	3	10.00	67%	33%	0%
Florida	2025-02-01	Y	3	6.67	67%	0%	0%
Lower Mid-Atlantic	2025-02-01	Y	6	13.33	100%	17%	17%
Midwest	2025-02-01	Y	6	16.67	100%	50%	17%
North	2025-02-01	Y	3	13.33	67%	67%	0%
Northeast	2025-02-01	Y	5	12.00	60%	40%	20%
Pacific Northwest	2025-02-01	Y	2	10.00	100%	0%	0%
South Central	2025-02-01	Y	2	20.00	100%	50%	50%
Southeast	2025-02-01	Y	4	15.00	100%	50%	0%
UK	2025-02-01	Y	10	12.00	100%	20%	0%
Upper Mid-Atlantic	2025-02-01	Y	8	15.00	63%	63%	25%
Upstate NY	2025-02-01	Y	3	6.67	67%	0%	0%

Data


Valencia A	Florida State A	10	0	0	10
UCF B	Florida B	0	0	0	0
Florida A	UCF C	10	0	0	10
Brandeis A	Tufts A	10	0	0	10
BU	Brandeis B	0	0	0	0
Harvard A	Dartmouth A	10	10	0	20
Harvard B	MIT A	10	10	10	30
UMass Boston	Brown A	0	0	0	0
Columbia B	Maryland A	10	10	0	20
Cornell B	Haverford A	10	10	10	30
George Washington A	Vassar A	0	0	0	0
Maryland B	George Washington B	0	0	0	0
UNC C	Duke	10	10	10	30
Virginia Tech A	Liberty A	10	0	0	10
William & Mary	Liberty B	10	0	0	10
UNC B	South Carolina	10	0	0	10
Virginia A	Liberty C	10	0	0	10
UNC D	Wake Forest	10	0	0	10
Chicago B	Chicago C	10	10	0	20
Missouri	Chicago D	10	0	0	10
Indiana B	Illinois C	10	0	0	10
Indiana A	Illinois B	10	0	0	10
Bristol	Oxford C	10	0	0	10
Cambridge A	NYU C	10	10	0	20
Oxford A	Cambridge B	10	0	0	10
Manchester	Cambridge C	10	0	0	10
LSE	Cambridge D	10	0	0	10
Imperial A	Cambridge E	10	10	0	20
Warwick A	Durham	10	0	0	10
Imperial B	Warwick B	10	0	0	10
Sheffield	Southampton A	10	0	0	10
Southampton B	Oxford B	10	0	0	10
UC Berkeley B	Claremont A	10	10	0	20
Claremont B	UCLA	0	0	0	0
UC Berkeley A	UCSD	10	0	0	10
Illinois A	Missoui S&T	10	10	0	20
WashU B	Chicago A	10	10	10	30
Iowa State	Carleton	10	10	0	20
Minnesota B	Winona State	10	10	0	20
Wisconsin A	Wisconsin B	0	0	0	0
Alberta	UBC	10	0	0	10
UW A	UW B	10	0	0	10
ASU	TAMU	10	10	10	30
Texas A	Texas B	10	0	0	10
Louisville A	Georgia Tech B	10	0	0	10
Georgia Tech C	Georgia Tech D	10	10	0	20
Vanderbilt A	Georgia Tech A	10	0	0	10
Bruin A	Tennessee A	10	10	0	20
John Jay College	Haverford B	0	10	0	10
Johns Hopkins A	NYU B	10	10	10	30
Penn A	Penn B	10	0	0	10
Rutgers A	Yale A	10	10	0	20
Cornell C	Binghamton A	10	0	0	10
RIT A	Cornell D	10	0	0	10
ESF A	RIT B	0	0	0	0