Itunes will not send over the purchased music without syncing

having some seriously peculiar issues with itunes
the new phone shows all the music from my purchased ensemble, but it is grayed out and some  tunes sync over and most NOT
there are apprx 370 songs and 5 hrs later maybe 6 have synced over
what the heck is happening
i can't seem to get the phone to recognize the songs or visa versa...??
the summary page comes up, it just doesn't seem like everything is connecting somehow??
H E L P!!!
thankx

Why can you not redownload your previous purchases?

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