keeps saying it wont sync as duplicate name

I had my last Ipod stolen so brought myself a new one in December and it just sync'd fine. Now everytime I plug it in the pc it crashes and has twice deleted all my songs so I've had to sync again. It keeps crashing and I don't know why. I now don't get any album artworks and just names.

I have just plugged it back into the pc and it now keeps saying can't sync as duplicate name. I don't know how to combat this and I have uploaded the new software hoping that it would help but nothing.

I have no virus's on my pc as I have checked this. Really not happy as I never had any problems with my last Ipod and I had that over a year.