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organic chem Gringards question

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Mrhyde

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With A Terminal Alkyne, NaNH2 steals the H to make the Alkyne charged ......

But this is the first time that I see Gringards with a terminal Alkyne and apparently with a terminal Alkyne, Gringards will react the same way as NaNH2 ? is this unusual for Gringards to do this with a terminal alkyne, as i have only ever seen this with NaNH2?

Gringards:

https://d2gne97vdumgn3.cloudfront.net/api/file/cu9v2hZbRMSx1iIedurD

NaNH2:

http://11452-presscdn-0-51.pagely.netdna-cdn.com/wp-content/uploads/2011/07/example1-copy.jpg
 

russelldw

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No this is not unusual. The proton on a terminal alkyne will usually be pulled off by any strong nuc/base, including a gringard.
 

Mrhyde

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Thanks for the reply. Hmm I found it strange because in every single example i have ever seen thus far , NaNH2 seems to be the only one ever chosen to display a proton being removed from a terminal alkyne
 

russelldw

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Thanks for the reply. Hmm I found it strange because in every single example i have ever seen thus far , NaNH2 seems to be the only one ever chosen to display a proton being removed from a terminal alkyne
I would try to avoid memorizing specific reactants, and instead think about the characteristic of the reactants. For example, NH2- is a strong base so it will obviously pull off an acidic proton (such as a terminal proton on an alkyne). Other reactants that share this same characteristic will also pull the proton off (OH-, H-, Gringards, etc.)
 
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