Grignard reagents - 2025 ACF Winter

Question

These molecules are protonated by water, preventing the formation of a magnesium intermediate. For 10 points each:

[10m] What molecules are normally dissolved in nonpolar solvents like diethyl ether and contain both magnesium and a halogen? These species attach R groups to carbonyls through alkoxide intermediates.

ANSWER: Grignard reagents [or Grignard compounds]

[10h] Grignards are sometimes dissolved in this organic solvent that consists of a five-membered ring containing an oxygen. This solvent’s ether group strongly complexes to magnesium and it is also used in hydroboration reactions.

ANSWER: THF [or tetrahydrofuran; accept oxolane or 1,4-epoxybutane or 1-oxacyclopentane]

[10e] Water cannot be used in Grignard reactions as the reagents are strong examples of these hydrogen-accepting molecules. These molecules contrasted with acids also include sodium hydroxide.

ANSWER: bases [accept basic molecules; accept strong bases; accept Brønsted–Lowry bases; accept Lewis bases]

<Editors, Chemistry>

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Summary


California	Main	Y	5	22.00	100%	80%	40%
Canada	Main	Y	6	26.67	100%	83%	83%
Great Lakes	Main	Y	6	10.00	100%	0%	0%
Lower Mid-Atlantic	Main	Y	7	18.57	100%	57%	29%
Midwest	Main	Y	10	16.00	100%	50%	10%
North	Main	Y	10	20.00	100%	60%	40%
Northeast	Main	Y	5	18.00	100%	40%	40%
Pacific Northwest	Main	Y	9	17.78	100%	56%	22%
Pacific Northwest	Main	Y	1	30.00	100%	100%	100%
South Central	Main	Y	5	10.00	100%	0%	0%
Southeast	Main	Y	12	20.00	100%	67%	33%
UK	Main	Y	4	17.50	100%	50%	25%
Upper Mid-Atlantic	Main	Y	8	23.75	100%	75%	63%
Upstate NY	Main	Y	8	20.00	100%	50%	50%
2025 ACF Nationals	2025-08-09	Y	11	20.00	100%	73%	27%
2024 ARCADIA at UC Berkeley	04/19/2025	Y	4	15.00	100%	25%	25%

Data


Berkeley A	Berkeley D	0	0	10	10
Stanford C	Berkeley E	10	0	10	20
Berkeley C	Berkeley F	10	10	10	30
Stanford A	Berkeley B	10	0	10	20
Stanford B	UCSC	10	10	10	30
Claremont Scripps	UCSD Two Running Violet V Forms	10	10	10	30
UCLA D	UCI	10	10	10	30
UCLA A	UCSB	10	10	10	30
UCLA B	UCSD Vices and Virtues	10	10	10	30
UCLA C	UCSD What Hath God Wrought	0	0	10	10
USC	Claremont Pitzer	10	10	10	30
UF B	ERAU B	0	0	10	10
UF E	Melbourne B	0	0	10	10
ERAU A	UF C	0	0	10	10
FSU	UF D	0	0	10	10
UF A	USF	0	0	10	10
FIU	Melbourne A	0	0	10	10
CWRU C	Kenyon A	10	10	10	30
MSU A	CWRU A	10	0	10	20
OSU D	CWRU B	0	0	10	10
MSU B	OSU B	0	0	10	10
OSU C	OSU A	10	10	10	30
Pitt B	Pitt C	10	0	10	20
CWRU D	Kenyon B	0	0	10	10
Tennessee A	Clemson B	0	0	10	10
Liberty A	Tennessee B	10	0	10	20
Liberty C	North Carolina C	0	0	10	10
James Madison	North Carolina B	0	0	10	10
Virginia B	Roanoke	0	0	10	10
North Carolina A	South Carolina B	10	10	10	30
South Carolina A	Tusculum	10	0	10	20
Virginia A	NC State	10	0	10	20
Virginia Tech A	Clemson A	0	0	10	10
Virginia Tech B	Liberty B	10	0	10	20
Georgetown A	George Mason B	0	0	10	10
Maryland C	Georgetown B	10	10	10	30
George Washington A	Johns Hopkins C	0	0	10	10
Maryland A	George Mason C	10	10	10	30
Penn A	Maryland B	10	10	10	30
NYU A	Catholic University	10	10	10	30
NYU B	George Washington B	0	0	10	10
Notre Dame E	Johns Hopkins A	0	0	10	10
Penn B	Maryland D	10	0	10	20
VCU A	UMBC A	10	0	10	20
Columbia A	Princeton A	10	10	10	30
Swarthmore A	Columbia C	0	0	10	10
Vassar A	Lehigh A	0	0	10	10
Lehigh B	Rowan A	0	0	10	10
Rutgers B	Columbia B	10	10	10	30
Michigan A	Chicago D	10	10	10	30
Indiana A	Purdue C	10	10	10	30
Illinois A	Indiana B	10	0	10	20
Michigan B	Louisville B	0	0	10	10
Chicago A	Michigan D	10	0	10	20
UIC	Notre Dame B	0	0	10	10
Kentucky	Notre Dame D	10	0	10	20
Illinois B	Purdue A	0	0	10	10
Purdue B	Notre Dame A	0	0	10	10
Chicago C	Notre Dame C	10	10	10	30
Carleton	Minnesota C	0	0	10	10
Macalester A	Minnesota A	0	0	10	10
Macalester B	Iowa State	0	0	10	10
St. Thomas	Nebraska	0	0	10	10
Wisconsin	Minnesota B	0	0	10	10
Cornell-UG	Bowdoin B	10	0	10	20
Brown A	BC A	10	0	10	20
BC B	Brandeis Lloyd George	0	0	10	10
Brandeis Orlando	BU	0	0	10	10
Amherst A	Brown C	10	10	10	30
MIT A	Brown B	10	0	10	20
MIT B	Dartmouth	10	0	10	20
Tufts A	Amherst B	0	0	10	10
Brandeis Wilson	Tufts B	0	0	10	10
Williams	Bowdoin A	10	10	10	30
Harvard	Yale B	10	10	10	30
British Columbia A	Washington B	0	0	10	10
British Columbia D	Washington A	10	10	10	30
Simon Fraser	British Columbia C	10	0	10	20
British Columbia B	Alberta	0	0	10	10
Alberta B	UTD A	10	0	10	20
Arizona State A	Northwestern B	10	10	10	30
Northwestern A	Arizona State B	10	10	10	30
Tulsa	Ohio	10	10	10	30
Rose State	Iowa	0	0	10	10
McGill D	Texas A	10	10	10	30
Northwestern C	Texas B	0	0	10	10
UCO	UTD B	10	10	10	30
Yale A	Brandeis Clemenceau	10	10	10	30
Georgia Tech A	Alabama A	10	10	10	30
Auburn A	Georgia Tech B	10	0	10	20
Georgia Tech C	Alabama B	0	10	10	20
Vanderbilt B	Georgia Tech D	0	0	10	10
Vanderbilt A	Huntsville A	0	0	10	10
Bruin A	Huntsville B	10	10	10	30
Mississippi State A	Sewanee A	0	0	10	10
UAB A	Auburn B	10	10	10	30
Cambridge B	Imperial A	10	0	10	20
Sheffield B	Birmingham A	0	0	10	10
Durham B	Sheffield C	0	0	10	10
Edinburgh B	Warwick B	10	0	10	20
Imperial B	Edinburgh A	10	10	10	30
Bristol A	LSE B	10	0	10	20
Lancaster A	Bristol B	10	0	10	20
Southampton A	Manchester A	0	0	10	10
Cambridge A	Manchester B	10	0	10	20
Oxford A	Imperial C	10	10	10	30
Cambridge C	LSE A	10	10	10	30
RIT A	Rochester	0	0	10	10
ESF	Cornell-DII	0	0	10	10
RIT B	Binghamton B	10	10	10	30
Syracuse	Binghamton A	0	0	10	10