Purchased itunes do not show up on ipod

I can purchase music from itunes but when I transfer music to my ipod (5th gen) they are not on the ipod. I can upload music from cds and they transfer fine. I tried reseting but that did not help. Now what?
pc   Windows XP  

Try playing the songs on your computer. Do they play?
Also, are you automatically updating all songs and playists?
Try going to advanced-->deauthorize computer (in iTunes). Then play a purchased song. Enter your account info. Play a few songs for a few seconds. Update your iPod with iTunes. Do the songs transfer?
Finally, make sure everything is up to date...
iTunes
iPod Updater
Updating iPod's Software
btabz

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