Cannot add song to touch? Stated it could not be updated.

Two songs on my son's touch did not play completely, so I deleted them from the touch and then added them to his touch. One song works perfectly the other I cannot even get the touch to sync the song. After turning off the touch, computer, and changing the convert size, I finally got a message saying the song could not be updated. Is there anyway to get the song back on my son's touch?

Restore from backup

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