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Date: 7-9-2018
1134
Date: 3-8-2019
1012
Date: 25-9-2020
1241
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Hydrogen on a terminal alkyne is somewhat acidic, with a pKa of approximately 25. This means that, given a strong enough base, terminal alkyne can be deprotonated, yielding a powerful carbanion nucleophile, which we used in SN2 reactions. Sodium hydride, or sodium amide in liquid ammonia is often used for this purpose.
The alkynyl carbanion can then be combined with a suitable electrophile, such as a primary alkyl bromide, in a carbon-carbon bond-forming SN2 displacement reaction. However it can also add to polar bonds in the same way as a Grignard reagent, for example giving an alcohol when added to a ketone.
Grignard reagents will not react efficiently in SN2 reactions with alkyl halides (the Gilman reagent, described below, can be used for this purpose).
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