Resyncing Previously Downloaded Music to Ipod Touch?

I have a lot of music downloaded that I removed from my library a long time ago and I redownloaded it and am trying to sync it to my Ipod Touch 4th generation, but it doesn't sync? 

Update: The 12 songs were under a different account so that might be the problem.
Edit: The other purchased music mentioned in the previous post were songs from Amazon and not iTunes.
I just purchased a few songs from Amazon and didn't have any problem syncing those.
The free apps that I downloaded from iTunes synced and work just fine. I just bought my first song with my current iTunes account and the exact same thing is happening. The song shows up on the iPod but there's no sound. What am I doing wrong?

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