SN2 - Upstate NY - 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


Cornell D	Binghamton A	10	10
Cornell B	Binghamton B	10	10
Cornell A	Cornell C	10	10
ESF	RIT B	10	10
Rochester	RIT A	10	10