thalidomide - 2025 ACF Winter

Question

This drug’s single stereocenter can undergo chiral inversion at a nitrogen–carbon bond. For 10 points each:

[10e] Name this drug that was used to treat morning sickness that caused birth defects. The two isomers of this drug interconvert, although only the S isomer is biologically active.

ANSWER: thalidomide [or Contergan; or Thalidomid]

[10m] Thalidomide does not possess these isomers, which have more than one stereocenter, but remain superimposable. For two stereocenters, these optically inactive compounds have (R,S) (“R S”) configuration.

ANSWER: meso compounds

[10h] This form of spectroscopy uses the difference in absorption of polarized light. A vibrational form of this technique operates in the infrared, while a UV form can probe the secondary structure of proteins.

ANSWER: circular dichroism [or CD]

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Summary


California	Main	Y	5	12.00	80%	20%	20%
Canada	Main	Y	6	10.00	83%	17%	0%
Florida	Main	Y	11	12.73	100%	18%	9%
Great Lakes	Main	Y	4	10.00	75%	25%	0%
Lower Mid-Atlantic	Main	Y	5	6.00	60%	0%	0%
Midwest	Main	Y	8	7.50	63%	13%	0%
North	Main	Y	10	9.00	60%	30%	0%
Northeast	Main	Y	5	8.00	60%	20%	0%
Overflow	Main	Y	3	10.00	67%	33%	0%
South Central	Main	Y	5	8.00	80%	0%	0%
Southeast	Main	Y	9	13.33	89%	33%	11%
UK	Main	Y	4	15.00	100%	50%	0%
Upper Mid-Atlantic	Main	Y	7	15.71	71%	43%	43%
2024 ARCADIA at UC Berkeley	04/19/2025	Y	2	5.00	50%	0%	0%

Data


Berkeley B	Berkeley C	10	0	0	10
Berkeley F	UCSC	10	0	10	20
Stanford B	Berkeley A	10	10	0	20
Stanford C	Stanford A	0	0	0	0
UCSD What Hath God Wrought	USC	10	0	0	10
Guelph A	Carleton	10	0	0	10
McGill B	McMaster C	10	0	0	10
Toronto H	McGill C	10	0	0	10
McMaster A	Queen's A	10	10	0	20
Toronto Metropolitan	Ottawa	10	0	0	10
Toronto A	Toronto G	10	10	10	30
Toronto B	Guelph B	10	0	0	10
Toronto C	Toronto J	10	0	0	10
Toronto D	McGill A	10	0	0	10
Western Ontario	Toronto I	10	0	0	10
Toronto K	McMaster B	10	0	0	10
FIU	UF E	0	0	0	0
FSU	UF C	10	0	0	10
UCF B	UF B	10	0	0	10
UCF A	UF A	10	10	0	20
MSU A	OSU D	0	0	0	0
OSU A	CWRU B	10	0	0	10
OSU B	OSU C	10	0	0	10
Pitt A	CWRU A	0	0	0	0
Pitt B	Kenyon B	10	0	0	10
Claremont Scripps	UCLA D	10	10	0	20
UCLA B	UCLA A	10	0	0	10
Claremont Pitzer	UCLA C	10	0	0	10
UCSD Two Running Violet V Forms	UCI	0	0	0	0
UCSB	UCSD Vices and Virtues	10	0	0	10
Tennessee A	Clemson A	0	0	0	0
Virginia A	Liberty A	10	0	0	10
Liberty B	Liberty C	0	0	0	0
North Carolina A	North Carolina B	10	0	0	10
Virginia Tech A	South Carolina A	10	10	0	20
North Carolina C	South Carolina B	0	0	0	0
NC State	Tennessee B	10	0	0	10
Virginia Tech B	Virginia B	10	0	0	10
Berkeley D	Berkeley E	10	0	0	10
George Mason A	UMBC A	0	0	0	0
Maryland B	George Washington B	10	0	0	10
Georgetown B	Maryland D	0	0	0	0
Johns Hopkins A	George Mason B	10	10	0	20
Johns Hopkins B	Penn B	0	10	0	10
Johns Hopkins C	George Mason C	0	0	0	0
VCU A	Maryland A	10	0	0	10
Maryland C	NYU A	10	0	0	10
George Washington A	NYU B	10	0	0	10
Penn A	Georgetown A	10	10	0	20
Columbia A	Rutgers C	10	0	0	10
Lehigh A	Princeton A	10	0	0	10
Rutgers B	Rowan A	0	0	0	0
Swarthmore A	Vassar A	0	0	0	0
WashU A	Missouri B	10	10	0	20
WashU C	Missouri A	10	0	0	10
WashU D	SIUE	0	0	0	0
Macalester A	Minnesota B	10	0	0	10
Macalester B	Wisconsin	10	0	0	10
Minnesota A	Minnesota C	10	0	0	10
Nebraska	Iowa State	10	0	0	10
Carleton	St. Thomas	0	0	0	0
Amherst A	Dartmouth	10	10	0	20
Brown B	BC A	10	0	0	10
Brandeis Clemenceau	BU	10	0	0	10
Brandeis Wilson	Brandeis Lloyd George	10	0	0	10
Cornell-UG	Brown A	0	0	0	0
Brown C	MIT B	10	10	0	20
Yale A	MIT A	10	0	0	10
Tufts B	Bowdoin A	10	0	0	10
Harvard	Williams	10	10	10	30
Columbia B	Columbia C	10	10	0	20
British Columbia D	Alberta	10	10	0	20
British Columbia B	Washington A	10	0	0	10
Washington B	British Columbia C	10	0	0	10
British Columbia A	Simon Fraser	10	10	0	20
Arizona State A	Alberta B	10	10	10	30
Texas A	Arizona State B	10	0	10	20
McGill D	Iowa	0	0	0	0
Northwestern A	UTD B	10	0	10	20
Northwestern B	Northwestern C	10	10	0	20
Texas B	Ohio	10	10	0	20
Tulsa	UTD A	0	0	0	0
RIT B	Binghamton A	10	0	0	10
Rochester	Binghamton B	0	0	0	0