Question #a2287

1 Answer
May 28, 2015

The base will not remove the nitrile groups — it will convert them to carboxylic acids.

This is not an electrophilic aromatic substitution. It is a Diels-Alder reaction.

Furan reacts with dienophiles like maleic anhydride to form Diels-Alder adducts.

Both 1,1- and 1,2-dicyanoethene are also excellent dienophiles.

I assume that you are using the 1,2-isomer.

We can imagine it lining up to react with the furan:

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The product would be

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The NaOH hydrolyzes the nitrile groups to carboxylic acids.

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The final product is 7-oxabicyclo[2.2.1]hex-5-ene-2,3-dicarboxylic acid.