Im trying to sync my ipod but all it does is sync for an hour and then times out how do i fix this

I keep trying to sync my ipod because i have songs i put on there from cds that arent working they have a square with a circle around it and i cant play them so when i try to sync it it syncs and syncs forever and then finally says it cant be synced because my ipod timed out.  If anybody has any ideas that can help me out I'd greatly appreciate it.

Try:
- Reset the iOS device. Nothing will be lost
Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Unsync/delete all music and resync
To delete all music go to Settings>General>Usage>Storage>Music>Tap edit in upper right and then tap the minus sign by All Music
- Reset all settings      
Go to Settings > General > Reset and tap Reset All Settings.
All your preferences and settings are reset. Information (such as contacts and calendars) and media (such as songs and videos) aren’t affected.
- Restore from backup. See:                                                
iOS: How to back up                                                                                     
- Restore to factory settings/new iOS device.             

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