My songs on itunes will not upload on to my new 5th generation touch ipod

The songs I got off from youtube and converted on to itunes will not upload on to my new 5th generation i-pod? The message says that itunes can't find the songs. I have 387 songs from youtube and I don't want to have to convert them again.

The message means what it says. iTunes can't find the actual music files. You can confirm that by trying to play the songs in iTunes on the computer.
- Try:
iTunes: Finding lost media and downloads
- Next reimport them

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