4. (30 pts) Propose a synthesis route for the following conversion. Give the appropriate reagents needed (it may include more than one step).

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∻Solution∻ ‖ 1 ⋮ **Identify the starting material and product**: The starting material has a triple bond, which suggests it is an alkyne, and the product has multiple double bonds, indicating an alkene. The presence of a methyl group indicates that the starting material is a substituted alkyne. ‖ ‖ 2 ⋮ **Propose a synthesis route**: To convert an alkyne to an alkene with multiple double bonds, one possible route is to partially hydrogenate the alkyne to an alkene and then perform a reaction that introduces more double bonds into the carbon chain. ‖ ‖ 3 ⋮ **Step 1 - Partial Hydrogenation**: Use a catalyst such as Lindlar's catalyst to partially hydrogenate the alkyne to a cis-alkene. The reaction would be: $ ext{Alkyne} \xrightarrow{ ext{Lindlar's catalyst}} ext{cis-Alkene} $. ‖ ‖ 4 ⋮ **Step 2 - Formation of additional double bonds**: Perform an isomerization reaction to spread the double bonds along the carbon chain. This could be achieved using a strong base such as sodium amide ($ ext{NaNH}_2 $). The reaction would be: $ ext{cis-Alkene} \xrightarrow{ ext{NaNH}_2} ext{Poly-alkene} $. ‖ ∻Answer∻ ⚹ Step 1: Partially hydrogenate the alkyne using Lindlar's catalyst to obtain a cis-alkene. Step 2: Treat the cis-alkene with sodium amide to isomerize and form the poly-alkene with multiple double bonds. ⚹ ∻Key Concept∻ ⚹ Synthesis of poly-alkenes from alkynes ⚹ ∻Explanation∻ ⚹ The process involves partial hydrogenation of an alkyne to form a cis-alkene, followed by isomerization to spread the double bonds along the carbon chain. ⚹◊What reagents could be used to convert the organic compound with a triple bond and a methyl group into one with multiple double bonds and a methyl group branch?⍭ Generate me a similar question◊

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