Problems with I Tunes transfer from CD

So, I am trying to consolidate two libraries - one on my laptop which has music from CDs and the other a desktop which is where I have made most of my i tunes purchases. I made a back up disc from desktop and installed it on laptop. When I synced to my I-pod shuffle, only about half of the songs showed up on the Shuffle. When I tried to manually put the songs that didn't transfer onto the shuffle I am told that I am not authorized to play that song on the new computer. Why would some purchases transfer and some not? Thanks for any help - this is really frustrating.

When I tried to manually put the songs that didn't transfer onto the shuffle I am told that I am not authorized to play that song on the new computer
To authorize the song on the new computer, thereby allowing it to transfer to the shuffle, play one of them in iTunes.

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