SN2 - 2025 ACF Fall - Buzzpoints App

Question

This reaction mechanism occurs with an alkoxide ion and a primary alkyl halide in the Williamson ether synthesis. For 10 points each:

[10h] Identify this concerted reaction mechanism. A backside attack in this reaction mechanism results in a complete Walden inversion of stereochemistry.

ANSWER: SN2 [or bimolecular nucleophilic substitutions; prompt on SN or nucleophilic substitutions; reject “SN1” or “unimolecular nucleophilic substitutions”]

[10m] SN2 reactions are faster when performed with aprotic varieties of these molecules, such as acetonitrile or DMSO, since they shield the nucleophile less.

ANSWER: solvents [or aprotic solvents]

[10e] SN2 reaction rates also increase with the strength of the nucleophile, which is closely related to this property. Solutions with this property have a pH greater than 7.

ANSWER: basic [or alkaline; accept word forms like basicity or bases; accept word forms like alkali]

<Editors, Chemistry>

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Summary


Northern California	Main	Y	4	25.00	100%	75%	75%
Southern California	Main	Y	7	21.43	100%	57%	57%
Eastern Canada (1)	Main	Y	5	24.00	100%	80%	60%
Eastern Canada (2)	Main	Y	9	18.89	100%	22%	67%
Florida	Main	Y	4	12.50	100%	0%	25%
Great Lakes	Main	Y	11	20.00	100%	46%	55%
Lower Mid-Atlantic	Main	Y	9	22.22	100%	67%	56%
Upper Mid-Atlantic	Main	Y	12	19.17	92%	50%	50%
Midwest	Main	Y	9	14.44	100%	33%	11%
North	Main	Y	4	15.00	100%	25%	25%
Northeast	Main	Y	12	16.67	100%	33%	33%
Pacific	Main	Y	8	22.50	100%	63%	63%
South Central	Main	Y	7	15.71	100%	43%	14%
Southeast	Main	Y	13	14.62	100%	31%	15%
UK (North)	UK	Y	5	22.00	100%	60%	60%
UK (South)	UK	Y	8	18.75	88%	63%	38%
Upstate NY	Main	Y	5	10.00	100%	0%	0%

Data


Berkeley Archer Queen	Berkeley Boss Bandit	10	10	10	30
Berkeley Skeleton King	Stanford A	10	10	10	30
Berkeley Little Prince	UCSC	10	10	10	30
Claremont A	UCLA B	10	10	10	30
UC Irvine	UCLA E	10	10	10	30
UCSD A	UCLA A	10	10	10	30
UC Santa Barbara	UCLA F	0	0	10	10
UCLA D	UCSD B	10	10	10	30
USC A	Claremont B	0	0	10	10
Claremont C	USC B	0	0	10	10
Berkeley Mighty Miner	Stanford B	0	0	10	10
McGill A	Ottawa A	0	10	10	20
Ottawa D	Ottawa B	10	10	10	30
McGill B	McGill C	10	10	10	30
McGill E	Carleton B	10	0	10	20
Toronto I	Brock A	0	0	10	10
McMaster B	Guelph A	0	0	10	10
McMaster C	Queen's A	10	0	10	20
McMaster A	Toronto A	10	10	10	30
Toronto D	Toronto B	10	0	10	20
Toronto G	Waterloo C	0	0	10	10
Toronto H	Toronto F	10	0	10	20
Waterloo A	Toronto C	10	0	10	20
Waterloo B	Toronto E	10	10	10	30
ERAU Daytona A	South Florida A	0	0	10	10
Florida Tech A	Florida A	0	0	10	10
Florida B	UCF A	0	0	10	10
Florida State A	Florida Tech B	10	0	10	20
Carleton A	Ottawa C	0	10	10	20
CWRU A	Michigan D	10	10	10	30
CWRU B	CWRU C	10	10	10	30
Michigan State A	CWRU D	10	10	10	30
Kentucky	Michigan State D	0	0	10	10
Louisville A	Louisville B	10	10	10	30
Louisville D	Ohio State D	0	0	10	10
Michigan C	Louisville C	0	0	10	10
Ohio State C	Michigan State B	0	0	10	10
Michigan A	Michigan State C	0	10	10	20
Ohio State B	Pittsburgh	10	0	10	20
WVU B	Ohio State A	10	0	10	20
Duke A	William & Mary B	0	10	10	20
NCSU A	Virginia Tech B	10	10	10	30
NCSU B	Tusculum A	0	0	10	10
UNC A	William & Mary A	10	10	10	30
UNC D	UNC C	10	10	10	30
VCU A	Virginia Tech C	10	10	10	30
Virginia Tech A	Virginia A	10	10	10	30
William & Mary C	JMU A	0	0	10	10
Liberty C	JMU B	0	0	10	10
Johns Hopkins	Columbia A	10	10	10	30
Stony Brook	George Mason C	0	0	10	10
Lehigh A	Maryland C	0	0	10	10
NYU A	George Mason B	0	10	10	20
Vassar B	Penn	10	10	10	30
Maryland A	Princeton	10	10	10	30
Rowan	Columbia B	0	0	0	0
Rutgers A	Vassar A	0	0	10	10
Maryland B	Rutgers B	10	10	10	30
Rutgers C	NYU B	0	0	10	10
Rutgers D	George Mason A	10	10	10	30
Lehigh B	NYU C	10	0	10	20
WashU Grizzlers	Chicago B	0	0	10	10
Illinois Blue	Illinois Canada	10	10	10	30
William Woods University A	Illinois Champaign	0	0	10	10
Illinois Orange	Purdue C	0	10	10	20
Illinois Urbana	Iowa A	0	0	10	10
Indiana A	Purdue B	0	0	10	10
Chicago A	Indiana B	0	10	10	20
Iowa B	Purdue D	0	0	10	10
WashU Grolars	Rose-Hulman A	0	0	10	10
Michigan Tech	Minnesota	10	10	10	30
St. Thomas	Iowa State	0	0	10	10
Macalester	Wisconsin A	0	0	10	10
Wisconsin C	Wisconsin B	0	0	10	10
Amherst A	Williams B	0	0	10	10
Vermont A	Boston College B	10	10	10	30
Boston University B	Brandeis Beethoven	10	10	10	30
Vermont B	Brandeis Mozart	0	0	10	10
Brown A	Tufts C	0	0	10	10
Amherst B	Dartmouth A	0	0	10	10
Dartmouth B	Boston University A	10	10	10	30
Dartmouth C	MIT B	0	0	10	10
Tufts A	UConn A	0	0	10	10
Williams A	Southern Connecticut State University A	0	10	10	20
Brandeis Bach	Williams C	0	0	10	10
Boston College A	Tufts B	10	0	10	20
British Columbia A	Washington Atlantic	10	10	10	30
British Columbia C	Arizona State A	10	10	10	30
Washington Sockeye	Boise State	10	10	10	30
Texas	Arizona State B	10	10	10	30
Washington Coho	Washington Chinook	0	0	10	10
Alberta B	Washington Masu	0	0	10	10
Washington Pink	Washington State	10	10	10	30
Alberta A	British Columbia B	0	0	10	10
Tulsa B	Kansas State B	0	10	10	20
Rose State	Central Oklahoma B	0	0	10	10
Kansas State A	Harding	0	0	10	10
Tulsa A	Nebraska C	10	10	10	30
Oklahoma	Central Oklahoma A	0	0	10	10
Murray State College B	Nebraska A	0	10	10	20
Murray State College A	Nebraska B	0	0	10	10
Clemson A	Alabama A	0	10	10	20
Auburn B	Tennessee Tech	0	0	10	10
Vanderbilt B	Auburn C	0	0	10	10
Clemson B	Tennessee B	0	0	10	10
Montevallo	Clemson C	0	0	10	10
Emory A	Georgia Tech F	10	10	10	30
Georgia Tech E	Georgia A	0	10	10	20
Georgia Tech A	South Carolina A	0	0	10	10
Auburn A	Georgia Tech B	0	0	10	10
Georgia Tech D	Sewanne	0	0	10	10
Georgia Tech C	Tennessee A	10	0	10	20
Vanderbilt A	Chipola College	0	10	10	20
Mississippi State A	Vanderbilt C	0	0	10	10
Edinburgh C	Sheffield B	0	0	10	10
Edinburgh B	York	10	10	10	30
Durham A	Durham B	10	10	10	30
Edinburgh A	Durham C	0	0	10	10
Sheffield A	Durham D	10	10	10	30
Cardiff	Bristol	0	0	10	10
Cambridge A	Southampton	10	10	10	30
Birmingham	Cambridge C	0	0	10	10
Cambridge E	Oxford	10	10	0	20
Cambridge D	Imperial A	0	10	10	20
Warwick	LSE	0	0	10	10
Cambridge B	Imperial C	0	10	10	20
Cornell D	Binghamton A	0	0	10	10
Cornell B	Binghamton B	0	0	10	10
Cornell A	Cornell C	0	0	10	10
ESF	RIT B	0	0	10	10
Rochester	RIT A	0	0	10	10
Imperial B	Imperial D	10	10	10	30