Can't Sync Music to iPod Touch

I am having issues syncing or adding music to my iPod Touch. So here's what happened... I was adding new music to the iPod. I select an album and drag & drop it onto my iPod Touch in iTunes to sync the music onto my iPod. While it's syncing that album I drag and dropped another album to be synced. Once I did this all syncing ended. Afterwards I can't sync anything at all onto my iPod Touch.
I've restarted my iPod by holding the power button and home button at the same time. I've turned the device off by holding the sleep button in until it gives me the option to turn the device off. I've restarted iTunes too. The only thing that temporarily helped was updating to iOS 7.1.2, but afterwards the same issues persisted.
Specs
iOS 7.1.2
iTunes 11.2.2.3
iPod Touch 5th Generation
32 GB

hi there. thanks for responding. my answers underlined
What happens when you try to sync? it looks like it's working, but maybe it's just syncing from ipod TO imac not the other way round, not sure.
Was the iPod previous synced to another iTunes library/computer?
yes i think so. the imac is new to us, and previously i THINK the ipod was sync'd to our pc
Have you successfully synced from this iTunes library/computer before?
no
Do the songs play in iTunes?      
yes   
Do you have the right boxes checked to sync?
yes
does that narrow anything down ??
thanks again

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