Topic: Protonation of alkoxides (Read 5373 times)

am1001 · « **on:** October 12, 2011, 08:19:21 PM »

Hello,
Why can't alkoxides be protonated by strong acids? For instance, if you had a tertiary alkoxide and wanted to protonate it using sulfuric acid, why wouldn't that work? Wouldn't it still get the job done? I'm thinking that some sort of side reaction would happen, but I'm not exactly sure what.
Any advice you have would be greatly appreciated! Thanks

Honclbrif · « **Reply #1 on:** October 12, 2011, 08:53:43 PM »

I'm not sure where you heard that strong acids won't protonate alkoxides, because they will. Alkoxides are, in general, quite good bases.

Honclbrif · « **Reply #2 on:** October 12, 2011, 08:57:08 PM »

Just to clear things up, read up on pKa's.

Honestly, I've never heard of a Bronstead acid which won't react with a Bronstead base.

am1001 · « **Reply #3 on:** October 13, 2011, 01:26:25 AM »

I guess I phrased that very poorly...sorry about that

To clarify, I meant to ask why, in a Grignard reaction, it's a bad idea to use a strong acid to protonate alkoxides.
Sorry, I should have said that earlier -_-
Thanks!

Guitarmaniac86 · « **Reply #4 on:** October 13, 2011, 06:10:36 AM »

Possibly they would also dehydrate the final product, once it has been protonated. See elimination reactions

Topic: Protonation of alkoxides (Read 5373 times)

am1001

Protonation of alkoxides

Honclbrif

Re: Protonation of alkoxides

Honclbrif

Re: Protonation of alkoxides

am1001

Re: Protonation of alkoxides

Guitarmaniac86

Re: Protonation of alkoxides

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