I can't transfer music into my ipod

so everytime i drag songs to my music file on itunes, it just pops up but there's always the loading circle and it doesnt even load. it stays the grey colored font. And then when i try one song at a time, it finally goes through but the moment i transfer the next song into it, the first one won't work anymore and there's the caution sign next to the name of the song. After that no other songs will go through. It wont play on the ipod itself either.

The
Means that iTunes can't find the actual music file. TheiTunes index does not point to the correct location. Yu can verify that by trying to play the song in iTunes.
Try:
iTunes: Finding lost media and downloads
You can redownload iTunes purchases by:
Downloading past purchases from the App Store, iBookstore, and iTunes Store         

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