Alkylation of acetylides
2 real reactions from the literature, on metal acetylides. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Acetylide alkylation: acetylide ion (a metal acetylide), sodium ion and butyl bromide (a primary alkyl bromide) with Na; NH3 gives 1-hexyne (the terminal alkyne).
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Acetylide alkylation: 1-bromo-3-chloropropane (a primary alkyl chloride) and a metal acetylide with NH3 (l) gives 6-chlorohex-2-yne (the internal alkyne).