According to my book terminal alkynes are not observed in Birch reduction.Why is this so? The only property I know about them is that they are slightly acidic. Does this have something to do with it? Please help me understand this.

  • $\begingroup$ As Waylander has already mentioned, acetylide formation occurs instead: the introduction of this article clearly states this. @Hema Anyway, I am looking for a textbook with the mention that terminal alkynes are not suited for Birch reduction; would you mind telling me the name of the book you were looking at? $\endgroup$
    – domperor
    Jul 24 '20 at 5:13

The alkyne proton is acidic enough to react with the dissolving metal to give the anion, giving the metal alkynide as it shown by these procedures sodium acetylide prep, sodium phenylacetylide prep; this does not reduce.


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