[Penguinone]

Question: "Identify with reasons what products you would expect to obtain when 1-nitrocyclopentene is treated with KCN in Ethanol.

Attempt: ^-CN attacking carbon-2 and pi bond of carbon-carbon double bond breaking while new pi bond forms between carbon-1 and nitrogen and pi bond between nitrogen and oxygen breaks and lone pair arrives on oxygen. Ethanol acting a solvent.
I do not think my attempt is right due to the orbital orientation of the pi bonds.
Any help would be greatly appreciated. 

[zsinger]

That bond with a positive formal charge doesn't look happy .

[Penguinone]

That bond with a positive formal charge doesn't look happy .

Thank you for your reply. I've tried to make the formal positive charge happy but I've ended up with a really weird looking compound 
I assume the stereogenic centre (carbon-1) would be racemic?
NB. The nitrogen to carbon bond in the fifth drawing is a single bond.

Attempt 2:

[discodermolide]

The addition is correct but the electron pushing not.
In the intermediate after the addition of CN^- move the electrons back from the oxygen and let the C=N⁺ get a proton from the solvent to re-generate the nitro group.

[Penguinone]

Thank you so much for your reply discodermoldie.

Attempt 3: See Picture.

[discodermolide]

That looks a lot better.
In the second structure, as you move the electrons to make the C=N⁺ move the electrons in the N=O out towards the oxygen to give the O a full negative charge.