Hard Drive Crashed Having Problems Getting My Music Back

I completely lost my laptop hard drive. It was unsalvagable. Before I reinstalled Itunes on the new hard drive I plugged my Nano in and copied all of the music on it to a desktop folder as a backup. Then I reinstalled Itunes and plugged my Nano into the computer. I got a message that my Ipod was not recognized on this computer, or something to that effect, and did I want to associate it with my library, I clicked yes.
I can't get my music to play on the Ipod. My computer was able to recognize the music that I had put into the backup folder and I can add it to my libraries, and play it from Itunes but when I put it on the Ipod but it won't play. Oddly enough, two songs that I purchased a few years back will play on the Ipod but nothing else; they weren't on my Ipod Nano to begin with, they just showed up in my library when I added the new hard drive to my account.
Is there anyway to reauthorize all of the music or somehow make it play? It is possible to just uninstall Itunes, copy the desktop music files to the Ipod and then somehow start over, etc.?

I'm not sure I completely understand what you've done.
1) Did you back up the songs from your old hard drive? Those are your base files for songs purchased through iTunes, rather than those on the iPod. My understanding of Apple's DRM scheme is that the iPod is only intended to REFLECT what you have stored on your hard drive. Always a good idea to back up those hard drive files on an external drive, etc.
2) Once authorized, your iPod should play anything you are authorized to play on your main computer.
3) If you're trying to add those old files copied from your iPod back into iTunes, that may not be a possibility... Part of Apple's DRM scheme.
Hope any of this was helpful.
maz

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