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Topic: Preparation of an ether. Use of nBu[sub]4[/sub]NHSO[sub]4[/sub]  (Read 3109 times)

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Offline Fmeub

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Preparation of an ether. Use of nBu[sub]4[/sub]NHSO[sub]4[/sub]
« on: December 14, 2009, 05:28:59 AM »
Hi!

I actually just want someone to confirm whether my reasoning is correct.

Please look at the attachment.

The NaOH removes the proton of the secondary alcohol. The alkoxide then attacks the propargyl bromide in a SN2 fashion. The transition state of the SN2 reaction is stabilized by conjugation with the pi-bond of the alkyne.

I have tried looking for info regarding nBu4NHSO4. It seems it is a phase transfer catalyst. So I guess it means that it either brings the alcohol into the aqueous phase to be deprotonated, or it brings the NaOH into the organic phase?

Is this a named reaction? I don't seem to get a lot of useful information regarding this on Google.

Thanks!

Offline stewie griffin

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Re: Preparation of an ether. Use of nBu[sub]4[/sub]NHSO[sub]4[/sub]
« Reply #1 on: December 14, 2009, 08:28:22 AM »
As far as I know it's not a named reaction. However your reasoning and understanding of what's going on is correct. Good job  :).

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