Considering both stereochemistry and regiochemistry, which of the following methods is the best way to make the compound shown? Br CH3 H3C Br neither method is effective Li, NH3 Br HC-CEC-CH, both methods are effective H/Lindlar catalyst Br, H;C-CEC-CH2

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i need help figuring this out. I think it might be b but I'm not sure

Considering both stereochemistry and regiochemistry, which of the following methods is the best way to make the compound shown?
Br
CH3
H3C H
Br
neither method is effective.
Li NH3
Br2
H;C-CEC-CH,
both methods are effective
H/Lindlar catalyst
Br2
HC-CEC-CH,
Transcribed Image Text:Considering both stereochemistry and regiochemistry, which of the following methods is the best way to make the compound shown? Br CH3 H3C H Br neither method is effective. Li NH3 Br2 H;C-CEC-CH, both methods are effective H/Lindlar catalyst Br2 HC-CEC-CH,
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Explanation :

Since given reactant is trans addition of bromine on alkene .

Initially we have Li/NH3 so it can reduce alkyne to alkene and that too trans alkene .

And also in given reactant it must be trans alkene then after addition of Br2 anti addition of Brwould have been taken place at alkene .

But in case of H2/ lindlar catalyst ,alkyne will convert into cis alkene and after then addition of Br2 will take place .

But according to given product alkene should be trans .

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