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When the isolated product 4 is treated with sodium ethoxide in ethanol it rearranges to 5 as shown:

enter image description here

My TA says that you need to start with a reverse Claisen at the ketone but I am not quite sure where to go from there. I do not know how to move the nitrile alpha to the carbonyl furthest from the methyl group.

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    $\begingroup$ Have the anion next to the CN attack the ketone. When the tetrahedral intermediate breaks down the anion of the ester leaves giving on workup 5 $\endgroup$
    – Waylander
    May 22, 2018 at 20:09
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    $\begingroup$ A good exercise to solving this type of problem is trying to map the carbons of the reactant onto the carbons of the product. $\endgroup$
    – Zhe
    May 22, 2018 at 20:19

1 Answer 1

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Following is a reasonable suggestion for the rearrangement:

Acid catalyzed rearrangement

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