My music wont sync from my computer to my ipod

Question

I recently added some music from my sister's library onto my library through a file. It is in my library and available for listening, but there are no cloud symbols next to it saying that it is available in icloud, and whenever i try to sync my ipod, it says that it is syncing but does not sync. I have tried syncing it multiple times. When i go to my ipod on itunes next oto summary where it says 'music' and "sync all music', it only syncs about 300 of my songs (i have almost 600.) does anyone know how i can get these songs onto icloud or get my ipod to sync??? please this is urgent.

Answer 1

Only iTunes purchased music can hava a cloud icon and then only if the music was purchased with the account listed in Settings>iTunes and App Store on the iPod.
Was the iPod previous synced to another iTunes library/computer?
Have you successfully synced from this iTunes library/computer before?
If so have you done anything like update iTunes on the computer since it last successfully synced?
Do the songs play in iTunes?          
Does any media now sync to the iPod?
Do you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod       
Try syncing using the manual method                
Managing content manually on iPhone, iPad, and iPod