Please help.  Music files missing from itunes and computer!

I know that this isn't exactly a new issue, but I have scanned the discussions and nothing that I have read seems to help. My son has a nano (4th gen). He isn't sure but he thinks that maybe he disconnected his ipod before a sync was complete or something because all the music was deleted from it. He's not positive that's what happened but that's his best guess. No problem -- thought we'd just pull songs over again to it from our library. However, when we try to do this, on about 50% of the songs he wants (all were purchased, not from CDs) there are exclamation points next to the songs when we try to drag them and it says the file can't be found. I have looked in the itunes library on our computer and while I can find the libraries, they also don't have these specific songs we are looking for. I've tried to search and I just come up empty. Is there anything we can do beside buy the songs again? There are about 16 songs or so. A couple of them I have on my itouch. Could I somehow transfer the couple of songs to the computer? And would that work to get them to his ipod? Any help would be greatly appreciated.

+It appeared to do that as there are now duplicates in our library, but when I tried to drag the new song to the ipod, that darn exclamation appeared again and the song wouldn't transfer.+
It's easy to get rid of the duplicates. iTunes menu > View > View Options
Check the Date Added box, then click on the column name Date Added twice. Eveything you added to day will be at the top.
Then click File > Show Duplicates and only delte the one from today.
Do NOT delete both duplicates, or the song will be entirely gone.
As for dragging songs to the ipod, it has to be set for "manually manage music" for that to work. I don't understand about the exclamation point showing up again, unless you were dragging the 'old' reference that got deleted. Tyr dragging over the copy from today.

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