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Topic: secondary alkyl halides and SN2/SN1  (Read 1610 times)

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Offline rafs

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secondary alkyl halides and SN2/SN1
« on: May 07, 2015, 03:57:25 PM »
Solomons & Fryhle stated in their book that secondary alkyl halides are more likely to undergo SN2 reactions with weak bases and E2 with strong bases.

I understand SN1 and E1 occur better with weak bases than SN2 and E2... And I know it's better to avoid SN1 because other products may be found (if you can form a tertiary carbocation by rearrangement).

But if you don't have the possibility of rearrangement, why does secondary alkyl halides give mainly SN2 than SN1 with weak bases?

Offline Schrödinger

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Re: secondary alkyl halides and SN2/SN1
« Reply #1 on: May 13, 2015, 09:45:21 AM »
We are comparing two competing reaction mechanisms here. When a base reacts with an alkyl halide, both SN2 and E2 are possible.

But what property of the reagent (base) determines whether SN2 or E2 happens preferentially?
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