Can't copy all songs to ipod

Recently downloaded an album and tried copying it to my ipod and only half the songs copy? I've tried removing all songs and readding them and they still won't copy. In the itunes library under my ipod its saying they're all on there but when i use my ipod out of itunes they don't show up?

So you can sync apps and other media to the iPod?
Do you have the right boxes/items checked to sync?
Could you sync music from this iTunes library before?
What exactly happens when you try to sync?

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