What Causes Music Not To Play On My iPod Touch OS5.0.1 and Mac Pro?

I have an iPod touch and a Mac Pro.  I am running the latest iTumes and IOS.  About half my songs refuse to play either on the MacPro or the iPod.  None of the songs were purchased from the iTunes store.  This is a recent behavior.  The songs will also list songs out of order.  It will list one song and play another.  Everything is out of sync.  When I synced the iPod duplicate files were installed.  I fixed that but most of my songs will not Play.
iPod 4
iOS 5.0.1
Mac OS 7.2
iTunes 10.5.1

The app, if not restricted, may be hidden in your folders.  If you go to settings, general, reset, reset home screen layout, you can rule that out.
Does your restore give you a specific error?  If so, see http://support.apple.com/kb/TS3694 and http://support.apple.com/kb/TS1275
You can also restore from your iPod, by going to settings, general, reset, reset all content and settings, but make sure that you have created a backup beforehand.
About iTunes backups:
http://support.apple.com/kb/HT4946
About iCloud backups:
http://support.apple.com/kb/HT4859
If you are still having issues, you can always try to contact AppleCare
Seth

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