Assuming that all the following compounds are available, devise the best method to synthesize the target molecule indicated. Note that the "best method" refers to a route, where the target molecule is obtained at the highest yield with the least amount of side (unwanted) products. Show the mechanism of the reaction using curly arrows. 2. CH3I ONa CH;ONa FOCH3 target molecule

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Assuming that all the following compounds are available, devise the best method to synthesize the target
molecule indicated. Note that the "best method" refers to a route, where the target molecule is obtained at
the highest yield with the least amount of side (unwanted) products.
Show the mechanism of the reaction using curly arrows.
2.
CH3I
ONa
CH;ONa
OCH3
target molecule
Transcribed Image Text:Assuming that all the following compounds are available, devise the best method to synthesize the target molecule indicated. Note that the "best method" refers to a route, where the target molecule is obtained at the highest yield with the least amount of side (unwanted) products. Show the mechanism of the reaction using curly arrows. 2. CH3I ONa CH;ONa OCH3 target molecule
Expert Solution
Step 1

The target molecule is an ether. The ether is synthesized by the reaction of an alkyl halide with sodium alkoxide. The reaction proceeds via the SN2 reaction mechanism. 

The SN2 reaction always competes with the E2 elimination reaction. The ratio of substitution to elimination depends on the substrate alkyl halide.

  • Primary alkyl halide gives the substitution reaction in a good yield.
  • Tertiary alkyl halide gives the elimination reaction in a good yield.
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