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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Sandra on February 22, 2008, 12:15:59 AM

Title: Why is 1,4-benzoquinone considered an electrophile?
Post by: Sandra on February 22, 2008, 12:15:59 AM

I have been reading quite a bit about 1,4-benzoquinone and it has been labeled as an electrophile everywhere I read. By looking at the structure of 1,4-benzoquinone it is not very obvious to me why it would be considered an electrophile. I am aware of the definition of an electrophile, but I still don't see how 1,4-benzoquinone is an electrophile.

sandra

Title: Re: Why is 1,4-benzoquinone considered an electrophile?
Post by: adam on February 22, 2008, 04:17:50 AM

Hi, looking the structure the molecule is multifunctional.

-Ketone (reacts with hard nucleophiles)
-alkene with a electron withdrawing group (the ketone), reacts with soft nucleophiles.

-also is an oxidant, and is commonly used to reoxidize Pd (0) to Pd (II), in Pd (II) catalyze 1,4 additions of Nucleophiles to 1,3 diienes.

Hope it helps.

Adam.