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May 8, 2014 6:54 AM in response to Rovo1968by bobby_d,Hello Rovo1968,
Thank you for contributing to Apple Support Communities. It sounds like you are attempting to sync tracks in iTunes marked with an exclamation point. This indicates those tracks have been moved or removed at some point. It may be helpful to review this article which explains the symbols used in iTunes:
iTunes 11 for Mac: Symbols used in iTunes
http://support.apple.com/kb/PH12106
Exclamation point
Next to a song: The song can’t be located; it may have been moved or deleted.
Next to a podcast: Recent episodes haven’t been downloaded because you have multiple unplayed episodes.
You can collect those tracks into a playlist to isolate them, this article will guide you in finding and repairing those connections in the iTunes library:
iTunes: Finding lost media and downloads
http://support.apple.com/kb/TS1408
Cheers,
BobbyD