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#1 2010-04-26 15:48:39

orgopete
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Elimination of (1S,2R)-1-iodo-2-methyl-1-phenylbutane to E-butene

What is the E2 elimination product of the reaction of (1S,2R)-1-iodo-2-methyl-1-phenylbutane with sodium methoxide in methanol?

The preferred elimination occurs with anti-stereochemistry. Because this reaction is in methanol, the leaving group is a very excellent leaving group, the solvent is a polar methanol, some mechanistic leakage to an E1-elimination may occur, especially as the concentration of the reactant decreases and if it were to also deplete the methoxide. However, the problem does state to give the E2-elimination product so it should be as shown below.

         http://www.curvedarrow.com/chem/ZZ5B3839EA.jpg

Similar reactions are detailed in A Guide to Organic Chemistry Mechanisms.

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