Trouble with playing ourchased music on iPod

I just bought a new MacBook after my PC died.  I imported my iTunes music library on to the Mac, and everything plays perfectly. I reformatted my 160GB iPod Classic (it had been formatted for Windows) and then transferred all the music and playlists on to it. I have discovered that many songs just stop playing mid-song and it's dead silent or it skips to the next song. It ONLY happens with music that was purchased from iTunes. Last night I reformatted the ipod again, and again put all the music back. I have found that the problem was fixed for some songs, but now it's happening with many other songs off the purchased list. Suggestions would be welcomed.  thanks!

take a look at this
http://docs.info.apple.com/article.html?artnum=93014

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