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Songs won't sync - Offline playlist

I have been looking for hours on how to sync the songs that haven't been synced. Please help! Most of these songs that won't sync have been purchased from iTunes. Whenever I check my playlists on my iPhone it will say for example 378 out of 672 tracks synced. Whenever i try to click on the grey shaded songs an icon pops up that says "If you own the track, you can sync it from the compiter" Well I can't sync it from the computer because it won't work and I felt like I have tried everything. Does anyone have any ideas?

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