I create a playlist with songs that I purchased from itunes and when I try to sync it to my iphone some of the songs are missing but when I go to the playlist in itunes the song is there.  What could be happening?  What am I doing wrong?

I've created playlists with songs I've purchased from iTunes and also added songs I've purchased from iTunes to existing playlists.  Everytime I go to sync the playlist to my iPhone I find some of the new songs missing from the playlist.  I've deleted the playlist from the phone and reinstalled it.  I don't know what I"m doing wrong. Anyone have any idea what could be the problem?

Wondering if you haven't been bitten by the new "feature" of iOS 5, as was my son. turingtest2 explained it very well in reply to my own query about "missing" songs in playlists.
Here's that thread...
https://discussions.apple.com/message/16903613#16903613

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