Why can i not sync my Ipod music?

I purchased songs on my Ipod touch, but when i tried to sync it to my computer, it got rid of my songs (over 100) that i got from the itunes app. The app wont let me re-download the songs without paying for them agian. What is going on??

What ahppens when you try?
Was the iPod previous synced to another iTunes library/computer?
Have you successfully synced from this iTunes library/computer before?
Do the songs play in iTunes?
Do you have the right boxes checked to sync?
  iTunes: Syncing media content to iOS devices and iPod

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