I recently bought a few new songs from iTunes and they transfer to my iPhone, but not into the Playlists I dragged them into

I recently bought a few new songs from iTunes and they transfer to my iPhone, but not into the Playlists I dragged them into

Do the problem songs play in iTunes on the computer?
Is Settings>iTunes and App Store signed into the account that purchased them?
Can yo redownlod them directly to the iPod by:
Downloading past purchases from the App Store, iBookstore, and iTunes Store         
Do they show up in the Purchased list?
Do you have any Restrictions (Settings>General>Restrictions) set that would prevent syncing/loading those songs?

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