CH_3 - C equiv C - CH_3 xrightarrow[CH_3COOH] | vedclass

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Question

(D) The reaction of an internal alkyne with $BH_3$ in $THF$ followed by treatment with acetic acid $(CH_3COOH)$ is a stereoselective reduction process

Vedclass · Accepted Answer

$	ext{cis}-2-	ext{butene}$

Vedclass · Answer

(D) The reaction of an internal alkyne with $BH_3$ in $THF$ followed by treatment with acetic acid $(CH_3COOH)$ is a stereoselective reduction process.$1$. Hydroboration of $2$-butyne $(CH_3 - C \equiv C - CH_3)$ with $BH_3$ involves $syn$-addition to form a vinyl borane.$2$. Subsequent protonolysis with $CH_3COOH$ replaces the boron group with a hydrogen atom, retaining the $syn$ stereochemistry.This sequence converts the alkyne into a $cis$-alkene. Therefore, the major product is $	ext{cis}-2-	ext{butene}$.

$CH_3 - C \equiv C - CH_3 \xrightarrow[CH_3COOH]{BH_3, THF} \text{Major product}$

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