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15240672380's Question
Posted 3 months ago

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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Answer from Sia
Posted 3 months ago
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
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
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: AlkyneundefinedLindlar’s catalystcis-Alkene \text{Alkyne} \xrightarrow{\text{Lindlar's catalyst}} \text{cis-Alkene}
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 (NaNH2 \text{NaNH}_2 ). The reaction would be: cis-AlkeneundefinedNaNH2Poly-alkene \text{cis-Alkene} \xrightarrow{\text{NaNH}_2} \text{Poly-alkene}
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
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.

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