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Question

Which set of reagents(in the correct order)would accomplish the following transformation?

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Solution

Soda amide in liq ammonia abstracts acidic proton from alkyne to form carbanion which attacks methyl iodide. In the next step, hydrogenation with Lindlar's catalyst gives cis alkene.
Thus, the correct sequence is NaNH2/NH3(I);CH3I followed by H2//Lindlar catalyst.

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