Help, my iPod doesn't sync all my music

Ok, I transfered my music from my old pc to my new mac, via my ipod. One problem when I went to sync my music back onto my ipod not all the music would sync. This message keeps appearing,
Some of the items in the itunes library were not copied to
the ipod because you are not authorized to play them on this
computer.
I've tried authorizing my mac, but it doesn't seem to do anything. What am I missing? Is there something else I can do? There are 100 songs that won't sync, most of which I purchased from the itunes store.
Please help, and thanks in advance to anyone who can help out.

After fiddling with my itunes library i was able to authorize my computer, and then succesfully synced my ipod, thanks anyway

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