Hey There rgrady49,
It sounds like you may have some corrupted music files in your iTunes library that have been synced to your iPod. If you purchased the music from the iTunes Store, you can delete the songs, redownload them to your iTunes library, and resync them to your iPod.
If you did not purchase the music from the iTunes Store, then you would want to delete the songs, and reimport them from your CDs.
The following resources will explain these options in more detail.
Delete songs, playlists, or other items - iTunes Help
http://help.apple.com/itunes/mac/12/#/itns2945
Download past purchases from iTunes in the Cloud - Apple Support
https://support.apple.com/en-us/HT201272
Add music to iTunes - Apple Support
https://support.apple.com/en-us/HT201169
iTunes 12 for Mac: Sync iPod, iPhone, or iPad
https://support.apple.com/kb/PH19458?locale=en_US&viewlocale=en_US
I hope this information helps ....
- Judy