I was confronted with the reaction of 1-bromo-1-phenylethene with two equivalents of LDA, then the product is hydrolyzed. As it is a bulky base, it will surely deprotonate and form the phenylacetylene, and form phenylacetyl-lithium in a second step, but what happens when it is hydrolyzed? Will the product stay as it is or what happens?

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    $\begingroup$ The phenyllithium acetylide is a reasonably stable species (pKa mid 20s). Protonation will give phenylacetylene. $\endgroup$
    – Waylander
    Sep 16 '21 at 12:05

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