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Author Topic: USNCO 2014 Q58 - comparing rate of SN1 vs SN2 reactions  (Read 512 times)

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georgetian3

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USNCO 2014 Q58 - comparing rate of SN1 vs SN2 reactions
« on: January 09, 2019, 01:18:02 PM »

The reaction between which pair of reactants occurs the fastest for [OH-] = 0.010 M?

(A) CH3CH2CH2CH2Cl + OH-
(B) (CH3)3CCl + OH-
(C) CH3CH2CH2CH2Br + OH-
(D) (CH3)3CBr + OH

First looking at the leaving group, Br- is a better leaving group than Cl-, hence options A) and B) were removed.

I then thought that, as OH- is a strong base and a strong nucleophile, the reaction should occur through SN2 pathway, which is fastest in primary alkyl halides, hence C)

However, the answers state D). Why would this be faster?
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AWK

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Re: USNCO 2014 Q58 - comparing rate of SN1 vs SN2 reactions
« Reply #1 on: January 09, 2019, 10:16:04 PM »

Some compounds react through E1 pathway.
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Babcock_Hall

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Re: USNCO 2014 Q58 - comparing rate of SN1 vs SN2 reactions
« Reply #2 on: January 10, 2019, 02:27:53 AM »

It may be that the problem is getting at the rate laws for SN1 vs. SN2.  The same logic holds for E1 vs. E2.
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