[lissydoll206]

Hi-
  This is my first post and I am trying to figure out how this reaction works, and what the product is.  Please see attached photo of reaction... any help would be greatly appreciated!

Thanks,
Melissa

[Will]

This looks like a Diels-Alder reaction to me.

[lissydoll206]

Ok, so if this is a diels alder reaction, the two double bonds will break and form methyl groups on the ring, right? And there will only be one double bond in the ring?

Then, the C=C-N, acting as a dienophile will break it's double bond and attach on the the positions as shown in the attached picture?

I still think I am wrong, but I think I am maybe getting closer?
My other idea is that a bicycloproduct will form.

Let me know if I am on the right track
  Thank you!

-Melissa

[Will]

I am no expert, I have only taught myself this from a book, but I don't think that would be the Diels-Alder product (certainly no methyl groups, but there will be only one double bond remaining). Take a look at how Diels-Alder reactions happen here or google Diels-Alder.

[lissydoll206]

Using that, this is what I come up with.

Is this close?

[Will]

Yup! Thats what I got.

[lissydoll206]

Aliright, now, to name it

The double bond gets 1st priority, so knowing that, would it be named:

4-cyano-[2.2.1]-bicyclooctene?

[lissydoll206]

Oops, I meant it to be a [2.2.2]bicyclooctene

[Will]

I think it would be 5-cyanobicyclo[2.2.2]octene, but I'm not 100% sure.

[lissydoll206]

Alrighty, well, thank you for all your help today!  I'm working on another problem as well, and depending how that goes, I might have another reaction posted later

Thanks again!

[Albert]

I would call it bicyclo[2.2.2]oct-5-ene-2-carbonitrile.

[Will]

Yeah, thats what ChemDraw calls it, but it recognises 5-cyanobicyclo[2.2.2]octene, and that sounds like a better name for it (although nitrile is a better name for -CN in organic chem).

[Albert]

Although nitrile is a better name for -CN in organic chem.

Yes, exactly. I tried the name you proposed too. However, according to my organic chem book, nitrile is better than cyano.
Last but not least, bicyclo[2.2.2]oct-5-ene-2-carbonitrile makes easier to understand the position of the double bond and the -CN group.

[movies]

The way I learned numbering for bicycles would give the name 5-cyano-bicyclo[2.2.2]octene, for what that's worth.