When i go to sync my ipod nano 5th generation i get an error saying "A duplicate file name was specified".  what do i do then?

I am trying to sync my iPod nano 5th generation to my computer and when i go to add music through iTunes i get the following message:
The iPod "X's iPod" cannot be synced.  A duplicate file name was specified.  Any ideas how to fix this?
On my computer (iMac) while in iTunes it is showing that the music is indeed on my iPod, but when i eject the iPod there is nothing there.

I have a 27" iMac with the latest version of iTunes.  I tried restoring my iPod and even removing and re-installing iTunes.  What eventually worked for me was plugging into my PC and restoring/reformatting it to work with my PC.  I don't know why it wouldn't work with my iMac, but now it seems to be working.

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