My songs show up in the iTunes library but not on my iPod

I had my songs on my iPod Touch 3rd Generation for and I plugged it in over night. The next day I went to my music on my iPod and it said "No content available. Download songs from iTunes" I went to iTunes on my Dell computer and they are all there. I got most songs back except for ones I recently purchased.

This might sound weird, but here's an idea which worked for me re music that was newly added to itunes and showed up in my ipod but wouldn't play - I simply played the tracks in itunes first, just a second of time or so will do it, not the whole track, then connect the ipod and sync again and this time they played - hope this helps.

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    I stumbled across this thread for the same issue.  I had 12 songs  that suddenly wouldn't sync from iTunes on my iMac to my iPhone 4. 
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    Per Winnits I also ended up deleting them and downloading them to resolve the issue.
    I took a screenshot of the error window ("Some of the items in the iTunes library were not copied to the iPhone "My Name iPhone" because one or more errors occurred.") showing a list of the songs.  Then I disconnected my iPhone.
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    Hope that helps anyone that follows!

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