Songs wont work on ipod, but works on iphone

hello, my songs wont work on my ipod but it works on my iphone. is there a reason this is happening? the songs are in .aiff format.
i downloaded a bunch of songs from youtube, and used audacity to convert them because i didnt like the bit rate.
i think it's the 6th gen ipod nano? its the small square one with a touch screen.
after that, i synced my iphone and the ipod nano. the songs are working on my iphone, but not on my ipod nano..

That is a problem with iOS 5 and iTunes 10.5/10.6 for many users. Sometimes unsyncing the songs and resyncing works. Other times restoring from backup works. Other users had not really found a solution.

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