formyl group - 2026 ACF Regionals

Packet E: Bonus 13

This functional group can be added to arenes (“AIR-eens”) using the Vilsmeier–Haack reagent, which is formed in situ from phosphorus oxychloride and DMF. For 10 points each:

[10h] Name this functional group added to phenols using chloroform and a strong base in the Reimer–Tiemann reaction. An industrial process for adding this functional group to alkenes uses rhodium complexed to sodium salts of sulfonated triphenylphosphine.

ANSWER: formyl group [accept formylation or hydroformylation; accept aldehyde; accept CHO or COH; prompt on carbonyl or CO] (The industrial process is the Ruhrchemie/Rhone–Poulenc process, and the ligand is TPPTS.)

[10m] Deprotonating chloroform generates these compounds for EAS (“E-A-S”) in the Reimer–Tiemann reaction. Lone pairs of the N-heterocyclic type of these compounds coordinate ruthenium in Grubbs catalysts used for olefin metathesis.

ANSWER: carbenes [accept N-heterocyclic carbenes or NHCs; accept persistent carbenes; accept dichlorocarbenes]

[10e] The Reimer–Tiemann reaction has largely supplanted Gattermann–Koch formylation for the production of salicylaldehyde (“SAL-uh-sill-aldehyde”) due to the latter’s use of this toxic gas that competes with O2 for binding to hemoglobin.

ANSWER: carbon monoxide [or CO]

<AL, Chemistry> | Packet E - Chicago A, Toronto B, Brandeis B, JHU A

Heard	PPB	E %	M %	H %
75	10.13	91%	7%	4%

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Conversion

Team	Opponent	Part 1	Part 2	Part 3	Total	Parts
Alabama A	WashU B	0	0	0	0
Alabama B	Sewanee	0	0	10	10	E
Berkeley B	Stanford B	0	0	10	10	E
Berkeley C	Stanford A	0	0	10	10	E
Berkeley D	Berkeley A	0	0	0	0
Birmingham	Montpellier	0	0	10	10	E
Brandeis A	Southern Connecticut State	10	0	0	10	H
Bristol	Cambridge B	0	0	10	10	E
Brock	UBC B	0	0	10	10	E
CWRU A	Michigan State	0	0	10	10	E
Cambridge A	Warwick A	0	0	10	10	E
Cardiff	Southampton B	0	0	10	10	E
Carleton College	Missouri B	0	0	10	10	E
Catholic	Johns Hopkins B	0	0	10	10	E
Central Florida A	Florida A	0	0	10	10	E
Chicago B	Northwestern D	0	0	10	10	E
Chicago C	Chicago E	0	0	10	10	E
City St. George's	Cambridge C	0	0	0	0
Columbia A	Maryland C	10	0	10	20	HE
Columbia B	Maryland B	0	10	10	20	ME
Cornell A	RIT	0	0	10	10	E
Cornell B	Binghamton B	0	0	10	10	E
Cornell C	Penn State	0	0	10	10	E
Dartmouth B	Dartmouth A	0	0	0	0
Duke	VCU	0	0	10	10	E
Edinburgh A	Manchester	0	10	10	20	ME
Edinburgh B	Durham	0	0	10	10	E
Florida B	Central Florida C	0	0	10	10	E
Florida C	Central Florida B	0	0	10	10	E
Georgia Tech A	Missouri A	0	0	10	10	E
Georgia Tech B	Louisville A	0	0	10	10	E
Harvard A	Brown	10	0	10	20	HE
Harvard B	Bowdoin B	0	0	10	10	E
Illinois A	Notre Dame B	0	10	10	20	ME
Illinois B	Indiana C	0	0	10	10	E
Imperial A	Oxford A	0	10	10	20	ME
Imperial B	Southampton A	0	0	10	10	E
John Jay	NYU C	0	0	10	10	E
Kentucky	WashU A	0	0	10	10	E
LSE	UCL	0	0	10	10	E
Liberty A	James Madison A	0	0	10	10	E
Liberty B	North Carolina C	0	0	0	0
Louisville B	Vanderbilt B	0	0	10	10	E
Maryland A	Rutgers A	0	0	10	10	E
Michigan A	Ohio State A	0	0	10	10	E
Michigan B	Ohio State C	0	0	10	10	E
Minnesota A	Claremont	0	0	10	10	E
Mississipi State	Georgia Tech D	0	0	10	10	E
Murray State A	Texas A&M A	0	0	10	10	E
NC State B	Liberty C	0	0	10	10	E
NYU B	Vassar	0	0	10	10	E
North Carolina A	South Carolina B	0	0	10	10	E
Northwestern C	Northwestern B	0	0	10	10	E
Notre Dame A	Indiana A	0	0	10	10	E
Ohio State B	CWRU B	0	0	10	10	E
Oxford B	Imperial C	0	0	10	10	E
Oxford C	Warwick B	0	0	10	10	E
Pittsburgh	Michigan C	0	0	10	10	E
Purdue A	Illinois C	0	0	10	10	E
Purdue B	Indiana B	0	0	10	10	E
Rochester	Binghamton A	0	0	10	10	E
Rutgers B	Georgetown	0	0	10	10	E
South Carolina A	North Carolina B	0	0	10	10	E
Swarthmore	Columbia C	0	0	10	10	E
Tennessee A	Georgia Tech C	0	0	10	10	E
Texas A	Texas B	0	0	10	10	E
UC Santa Barbara	UCSD A	0	0	0	0
UCLA A	UCSD C	0	10	10	20	ME
UCLA B	UC Irvine	0	0	10	10	E
UCSD B	Arizona State	0	0	10	10	E
Virginia Tech A	NC State A	0	0	10	10	E
Wake Forest	Virginia	0	0	10	10	E
Washington A	Iowa State	0	0	10	10	E
William and Mary	James Madison B	0	0	10	10	E
Yale	Bowdoin A	0	0	10	10	E

Summary

Tournament	Edition	Match	Heard	PPB	E %	M %	H %
California (North)	Main Site	✓	3	6.67	67%	0%	0%
California (South)	Main Site	✓	4	10.00	75%	25%	0%
Canada	Main Site	✓	1	10.00	100%	0%	0%
Florida	Main Site	✓	3	10.00	100%	0%	0%
Great Lakes	Main Site	✓	5	10.00	100%	0%	0%
Lower Mid-Atlantic	Main Site	✓	9	8.89	89%	0%	0%
Midwest	Main Site	✓	8	11.25	100%	13%	0%
Northeast	Main Site	✓	5	10.00	60%	0%	40%
Overflow	Main Site	✓	4	10.00	100%	0%	0%
South Central	Main Site	✓	2	10.00	100%	0%	0%
Southeast	Main Site	✓	7	8.57	86%	0%	0%
UK	Main Site	✓	12	10.83	92%	17%	0%
Upper Mid-Atlantic	Main Site	✓	8	12.50	100%	13%	13%
Upstate NY	Main Site	✓	4	10.00	100%	0%	0%