diastereomers - 2025 ACF Regionals

Question

Nomenclature of these compounds usually involves the terms “syn” and “anti” that are preserved by rotation around a single bond. For 10 points each:

[10m] Name these organic compounds that have multiple chiral centers, but unlike meso compounds, are not superimposable on their mirror images.

ANSWER: diastereomers [or diastereoisomers; prompt on stereoisomers; reject “enantiomers”]

[10e] The diastereomer nomenclature terms “threo” and “erythro” come from examples of these compounds called threose and erythrose. Dextrose is an alternate name for right-handed glucose, which is one of these biomolecules.

ANSWER: sugars [or saccharides]

[10h] Diastereoselective reactions are governed by this phenomenon, observed in chiral ketones by Donald Cram. Nguyễn Trọng Anh incorporated the Burgi–Dunitz angle to Hugh Felkin’s model of this phenomenon.

ANSWER: asymmetric induction

<MY, Chemistry>

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Summary


California	2025-02-01	Y	3	16.67	100%	67%	0%
Florida	2025-02-01	Y	3	3.33	33%	0%	0%
Great Lakes	2025-02-01	Y	6	10.00	50%	50%	0%
Lower Mid-Atlantic	2025-02-01	Y	6	8.33	83%	0%	0%
Midwest	2025-02-01	Y	6	11.67	83%	17%	17%
North	2025-02-01	Y	3	10.00	67%	33%	0%
Northeast	2025-02-01	Y	5	12.00	100%	20%	0%
Pacific Northwest	2025-02-01	Y	2	5.00	50%	0%	0%
South Central	2025-02-01	Y	2	15.00	100%	50%	0%
Southeast	2025-02-01	Y	4	7.50	75%	0%	0%
Upper Mid-Atlantic	2025-02-01	Y	9	10.00	67%	33%	0%
Upstate NY	2025-02-01	Y	3	3.33	33%	0%	0%

Data


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