aromaticity - 2025 Penn Bowl

Question

Performing mass spectrometry on analytes with this property can form unstable tropylium ions. For 10 points each:

[10m] Name this property possessed by acidic compounds used as the matrix in MALDI, such as sinapinic acid. Molecules with this property generate diatropic currents in NMR due to proton deshielding.

ANSWER: aromaticity [prompt on cyclic or rings]

[10e] Aromatic intermediates may form when compounds with this functional group undergo a McLafferty rearrangement during fragmentation. These functional groups are characterized by a carbon-oxygen double bond.

ANSWER: carbonyls [accept ketones or aldehydes]

[10h] The McLafferty rearrangement of carbonyls often competes with this type of fragmentation that breaks the neighboring carbon-carbon bond of the carbonyl to form a neutral radical and an acyl cation.

ANSWER: alpha-cleavage

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Summary


2025 Penn Bowl - BU	11/01/25	Y	4	2.50	25%	0%	0%
2025 Penn Bowl - CWRU	11/01/25	Y	3	6.67	67%	0%	0%
2025 Penn Bowl - Mainsite (UPenn)	11/01/25	Y	6	13.33	100%	33%	0%
2025 Penn Bowl - Murray State	11/08/25	Y	2	5.00	50%	0%	0%
2025 Penn Bowl - Northwestern	10/25/25	Y	4	12.50	75%	50%	0%
2025 Penn Bowl - Online	11/08/25	Y	2	5.00	50%	0%	0%
2025 Penn Bowl - Ottawa	11/01/25	Y	7	12.86	100%	29%	0%
2025 Penn Bowl - Stanford	10/25/25	Y	4	20.00	100%	75%	25%
2025 Penn Bowl - UK	11/01/25	Y	9	14.44	89%	56%	0%
2025 Penn Bowl - UNC	11/01/25	Y	3	13.33	100%	33%	0%
2025 Penn Bowl - WashU	11/01/25	Y	2	10.00	50%	50%	0%

Data


Brandeis	Brown	0	10	0	10
I've been running into you in my lead plumbocene what could have benzene	Yale	0	0	0	0
Harvard	MIT A	0	0	0	0
Ohio State A	Michigan A	0	10	0	10
CWRU	Ohio State B	0	10	0	10
Michigan C	Pittsburgh	0	0	0	0
MIT B	RIT	0	0	0	0
Columbia B	JHU B	0	10	0	10
JHU A	Maryland A	10	10	0	20
Maryland B	Maryland C	0	10	0	10
Mount Sinai	NYU A	0	10	0	10
John Jay	NYU B	0	10	0	10
Columbia A	Swarthmore	10	10	0	20
Central Oklahoma	Oklahoma	0	0	0	0
Texas B	Texas A	0	10	0	10
UChicago C	Purdue A	0	0	0	0
Purdue B	Illinois	0	10	0	10
Indiana	UChicago A	10	10	0	20
Northwestern A	Northwestern B	10	10	0	20
rusty shackleford	New Young Whigs of America	0	0	0	0
abg academy	Wake Up Paddington A Washington Mystery	0	10	0	10
#OpenToBuzz	Aweille Kevin Fan osti continue comme ça	0	10	0	10
Guelph perfomative male competition	Carleton A	0	10	0	10
McGill B	Toronto E	0	10	0	10
Ottawa 67s	McGill Fartlets	0	10	0	10
Toronto Sunshine Bubbles	Toronto Murder on the Rider Express	0	10	0	10
Toronto G	Toronto Operation PBSuccess	10	10	0	20
Waterloo you are crooked	Queen's is monitoring the situation	10	10	0	20
Berkeley A	Berkeley B	10	10	0	20
In Search of Lost Clues	Free Win	0	10	0	10
Stanford A	Berkeley C	10	10	10	30
The best time to buzz was twenty clues ago. The second best time to buzz is now	Stanford B	10	10	0	20
1. Wawa 2. Blank Street 151. Black Sheep at Kings Cross rail	Alas poor Warwick, I knew him Edinburgh	0	0	0	0
Knorr Stock Clue	Of Mice and Penn	10	10	0	20
Bristold	Paul Quifford, or, It Was a Dark and Stormy Tournament	0	10	0	10
Penn and the Art of Tossup-Bonus cycle Maintenance	question mark	10	10	0	20
Galactic Ombudsmen	Quiztian Bale in Ratman Begins	10	10	0	20
The Bit and the Penndulum	Chimp Brisket	10	10	0	20
Coughing Baby	Washed Scrubs	10	10	0	20
To buzz is to be perceived	why is it called a score clue if nobody scores points on it	0	10	0	10
Burnaburiash's Lapis Lazuli	Hail to the Sheaf	0	10	0	10
Planck Sinatra	UNC B	0	10	0	10
VT A	Wise Duke	10	10	0	20
VT B	UNC A	0	10	0	10
Truman State	WashU Bouba	0	0	0	0
WashU Kiki	VJ Edgecombe School of Interior Design - Edwardsville	10	10	0	20