Question

Show the most efficient synthesis of the product from the starting material. Show all reagents your need over each arrow, and draw all products and intermediates (do not combine steps). You do not need to show the mechanism for any steps. Show all molecules synthesized along the way, and pay attention to stereochemistry. If a racemic mixture is produced in any step, show both products formed. If you make a mixture of regioisomers in any of the steps, place a box around the compound you would separate from the mixture, and carry on with your synthesis assuming you can isolate the desired compound. Please note in problem (b) all carbons in the product must come from ethyl propionate, which is why I have drawn it out twice. Me ?? OEt OEt Me ?? (c) CH Ph CH3

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CH Enter ea Cl 2 NaH ·@fs Me H, NHL eH3 AH ph SH 1 0

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