Items in library cannot be copied to iPod as file cannot be converted

When syncing my ipod classic I get a message saying that a number of songs  can't be synced as the files can't be converted. Also if I attempt to play the same songs on my macbook I get a message saying they cannot be played because my computer is not aurhorised, but it is?

Hi there trikytrev!
I have an article here that can help you troubleshoot this issue:
iTunes repeatedly prompts to authorize computer to play iTunes Store purchases
http://support.apple.com/kb/ts1389
Thanks for using the Apple Support Communities. Have a good one!
-Braden

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