I am unable to drag and drop music onto my nano 6th gen!

I am unable to drag and drop music onto my nano 6th gen that I downloaded into iTunes from 2 CDs that I purchased. Older songs will still copy! Oddly, I CAN drag and drop them onto my old video iPod!

Yes! It is set up for manual management because I have way more music than will fit on my nano so I am only putting my favorites on it! It's just odd that the music on the 2 new CDs I downloaded into iTunes will not copy over! When I drag my songs to the playlist I made on my nano it acts like it is copying because I get the number of songs icon and the + sign indicating that it is copying but then the playlist is empty. The nano will say for a couple seconds that it is synchronizing but in the end nothing has transferred! If I take an older song and drag it into the playlist it does copy! Seem like it has to do with the new CDs being compatible with nano? I would really appreciate any advice! Thanks!

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