Unable to have iTunes purchases sync to iPod

I'm fairly new to iTunes, and started buying a few songs and an audiobook through iTunes. When I first purchased them they were on my iPod, but today when I try to charge my iPod to the computer I get the following error message:
"Some of the items in the iTunes library, including "Nothing at All", were not copied to the iPod because you are not authorized to play them on this computer."
Has anyone encountered this before? Why does this happen? And how can I get my purchases on my iPod? I have tried the five "R"s to no avail.
Thank in advance for your help!

In itunes top menu click on store. Under store it says authorize this computer. Authorize your account to play songs on your computer. If your computer is already authorized, deauthorize it and authorize it again.
here is the link for some help.
http://www.apple.com/support/itunes/musicstore/authorization/

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There's info here on setting up separate libraries and user accounts. You won't have to reload (or re-import) all the music, just copy it.
The reason I suggest separate accounts on the Mac is because if you have the two libraries under the same user account, iTunes will also open the last library that was open in that account, and you'll always have to be mindful of which library that is. If you open iTunes and find it's not your library, you'll have quit, relaunch holding the option key and select the other library.
No, you won't have to log in and out of the Mac. (If I'm understanding your question here.) Multiple accounts can be logged in at the same time. And with fast user switching, you can toggle between user accounts.
I'll admit that maintaining the two libraries gets a little tricky, because if you share all the same music, you'll have to add it to one and update the other. (That won't happen automatically.) But I think Home Sharing makes this much easier to do.
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Hello jose mariofromsan luis potosi,
I apologize, I'm a bit unclear on the exact nature of the issue you are describing. If you are saying that your iOS devices are not showing up in iTunes on your Windows computer, you may find the troubleshooting steps outlined in the following article helpful:
iPhone, iPad, or iPod not recognized in iTunes for Windows - Apple Support
On the other hand, if you are saying that your devices are only showing a Connect To iTunes icon screen, then this article may be more useful:
If you can't update or restore your iPhone, iPad, or iPod touch - Apple Support
Regards,
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Thanks for using Apple Support Communities.
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Managing content manually on iPhone, iPad, and iPod
http://support.apple.com/kb/HT1535
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Doublechecking. Have you tried the iTunes Store loads partially or returns "Error 306" or "Error 10054" section in the Specific Conditions and Alert Messages: (Mac OS X / Windows) section of the following document?
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Unable to have iTunes purchases sync to iPod

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