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Topic: Reaction of a Tertiary OH with HCN in an Ethanolic Solution?  (Read 2189 times)

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Offline chrisg120

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Reaction of a Tertiary OH with HCN in an Ethanolic Solution?
« on: July 19, 2015, 02:48:02 PM »
Been trying to figure this out for hours.  I am in Organic 1 and the teacher wants us to outline the mechanism for this reaction:

http://imgur.com/R7KwKH1

I'm thinking the Hydrogen from HCN hydrates the OH into an H20, and it turns into a leaving group. Then you have an SN1 reaction where the CN- comes in as a nucleophile and binds to the Central carbocation that is is left when the H20.  We're doing Acid/Base/SN1/SN2/Elimination/Addition/Rearrangement reactions currently.  I've been able to find nothing definitive online about the reaction of a weak acid with a tertiary alcohol.

Any thoughts?
« Last Edit: July 19, 2015, 03:01:33 PM by Arkcon »
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Offline Dan

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Re: Reaction of a Tertiary OH with HCN in an Ethanolic Solution?
« Reply #1 on: July 19, 2015, 05:19:14 PM »
Quote from: chrisg120 on July 19, 2015, 02:48:02 PM
I'm thinking the Hydrogen from HCN hydrates the OH into an H20, and it turns into a leaving group. Then you have an SN1 reaction where the CN- comes in as a nucleophile and binds to the Central carbocation that is is left when the H20.

Hydration is not the correct term, it is protonation, but otherwise your SN1 suggestion seems logical to me.

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