ITunes thinks it is syncing music onto my iPod and finishes sync without actually doing it and it is greyed out on "on this iPod" how can I add it properly?

My iTunes is doing the most frustrating thing.
I'm trying to sync a new album I've downloaded and every time I drag it across to my iPod (I manage my music manually) it begins to sync and then finishes almost instantly. Checking in the "on this iPod section" the music is there in that greyed out state with the dotted circles next to each item as if it were to sync but it never does it. Its so frustrating
I tried making it autofill from a playlist only containing the songs I was trying to add and receive the following message:
"iTunes cannnot add any songs to the iPod because it already contains all the song in (titled) playlist."
So it thinks the songs are on there but they're not actually synced.
If you'd like any further info it is an iPod touch 3G i believe, 32G, OS 6.1.6.
almost filled up but space is definitely not the issue. The files are MPEG audio files 320Kbs
For the record I hate iTunes and all its f**king antics there has to be a better way...

Alrite simple fix if anyones having the same problem sorry, just gotta delete all the greyed out material on your iPod and re - add it seemed to work

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