2, 4-hexadiyne (CH_3-Cequiv C-Cequiv C-CH_3) | vedclass

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(D) Step $1$: Reduction of $2, 4$-hexadiyne with $Li/NH_3$ $(liq)$ is a dissolving metal reduction which produces the trans-alkene. Specifically,it re

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$I$ and $III$

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(D) Step $1$: Reduction of $2, 4$-hexadiyne with $Li/NH_3$ $(liq)$ is a dissolving metal reduction which produces the trans-alkene. Specifically,it reduces the internal alkyne bonds to trans-double bonds,yielding $(2E, 4E)-2, 4$-hexadiene.Step $2$: The reaction of $(2E, 4E)-2, 4$-hexadiene with $1$ equivalent of $Cl_2$ in $CCl_4$ is an electrophilic addition reaction to a conjugated diene.Step $3$: Electrophilic addition to conjugated dienes can occur via $1, 2$-addition and $1, 4$-addition.Step $4$: $1, 2$-addition to one of the double bonds yields $4, 5$-dichlorohex$-2-$ene (Structure $I$).Step $5$: $1, 4$-addition across the conjugated system yields $2, 5$-dichlorohex$-3-$ene (Structure $III$).Therefore,the possible constitutional isomers are $I$ and $III$.

$2, 4$-hexadiyne $(CH_3-C\equiv C-C\equiv C-CH_3)$ is allowed to react with $Li$ in $NH_3$ $(liq)$. The product obtained is treated with $1$ equivalent of $Cl_2$ in $CCl_4$. Which of the following constitutional isomers are possible products?

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