Recently when I buy new tunes on iTunes, when I plug my phone into my iMac to sync, the new tunes don't show up in the "purchased" playlist. They are in my library, though. Sometimes I have had to sync a few times to get them to show up, the last tunes I purchased aren't on the playlist even though I've tried syncing many times. I deleted and re-installed the app, but that didn't solve the problem. iTunes looks like it's syncing the tunes, but they don't show up. I listen to my music through my phone, not my computer so it's frustrating!