My iPod won't sync at least half the music on my selected playlists

I just bought a 7th generation 160 gb iPod classic, and when I tried to sync my music to it, an error message came up and said it couldn't add this one song in my library (along with almost 16 gbs of other songs) and I can't figure out why it's doing this. This music did sync on my previous iPods and I'm not sure what the problem could be. Any input would be greatly appreciated, thanks.

If you have upgraded to the latest iTunes and add the music to this new iTunes, it maybe the problem.
Using iTunes, can you try to convert the music to iPod compatible format like MP3 or AAC, note that iTunes convert to play with the new devices iPhone, iPod Touch and iPad, which has a higher Audio quality than iPod Classic.
http://support.apple.com/kb/HT1550
Have a Nice day!
If it works don't fix it, unless you are working for Microsoft or Apple.

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