My itunes won't play on my ipod?

I have purchased itunes but they will not play on my ipod, they play on my computer but not the ipod! My other downloaded music will play on the ipod so why won't the itunes i've purchased? Any insight is appreciated. Thank You

After a long period of furstration, *I found a solution!*
I had a similar problem, all the songs I purchased throug iTunes would appear on my color display, then the song would skip to the next song or back to the menu. My other songs played fine and my purchased songs played in iTunes.
I tried:
* the 5 r's (reset, restore, retry...)
* Moving my library to the desktop and then deleting the iTunes Library database file
* Deauthorizing and Re-authorizing my computer
* Updating the software for iTunes and my iPod
* Manually updating my iPod songlist
* Trying a different USB port
* Buying a new song on iTunes and trying to load it onto my iPod
What worked in the end????
I uninstalled iTunes and iPod updater.
I reinstalled iTunes and iPod updater from my original CD.
I then restored my iPod to the original factory condition.
I was able to load all my songs at that point - I did NOT update any software.
I was very relieved to see that my library was still on my computer - even though I removed iTunes.
I hope this helps!
Dell Windows XP Pro

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Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
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My itunes won't play on my ipod?

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