SONGS WON'T COPY TO IPOD

For the first time (I've had iTunes and an iPod for a long time), I'm getting an error message when I sync my iPod that says that "[s]ome of the items in the iTunes library...were not copied to [my iPod] because you are not authorized to play them on this computer."
Umm, what the f---? Why is this happening?
There are 103 songs that won't copy, and at first glance it appears that the first 103 songs I ever purchased are the very 103 that won't copy onto my iPod.
Anyone have any ideas about what is going on here? I am reasonably sure that I haven't copied all 103 of these songs to disc 5 times, or whatever the limit is.
Thanks in advance to all who answer.
TW

b noir:
your initial reply, which at first seemed promising, has now taken me to a whole other level of difficulty. allow me to elaborate.
1) i have attempted to play one of the aforementioned purchased songs in my itunes library, per your advice (not on my ipod, but on my imac). upon doing so, i get the error message:
"This computer is not authorized to play "______." Would you like to authorize it? The message box displays the Apple ID and asks me for the password.
2) all well and fine, except that the email address which displays in the message box as my Apple ID is old and obsolete--way obsolete. So of course, if I enter my present password, it will not match this old ID.
3) i attempted to change this old ID to my present ID. when I did so, my present ID, which DOES match my present password (and, thus, which i DON'T want to change), showed up as the ID to change.
4) what do i do? at this point i'm stuck.

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    b noir:
    your initial reply, which at first seemed promising, has now taken me to a whole other level of difficulty. allow me to elaborate.
    1) i have attempted to play one of the aforementioned purchased songs in my itunes library, per your advice (not on my ipod, but on my imac). upon doing so, i get the error message:
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    For the first time (I've had iTunes and an iPod for a long time), I'm getting an error message when I sync my iPod that says that "[s]ome of the items in the iTunes library...were not copied to [my iPod] because you are not authorized to play them on this computer."
    Umm, what the f---? Why is this happening?
    There are 103 songs that won't copy, and at first glance it appears that the first 103 songs I ever purchased are the very 103 that won't copy onto my iPod.
    Anyone have any ideas about what is going on here? I am reasonably sure that I haven't copied all 103 of these songs to disc 5 times, or whatever the limit is.
    Thanks in advance to all who answer.
    TW

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    I think the most probable cause for this is that your iTunes is not authorized to play songs that is brought from the store. If this is the case go to Store>Sign In and login with your Apple ID and password. Then it should be able to sync. If you want to check how many computer is authorized with the account of the songs that won't sync to your iPod, you have to go to the iTunes Store -- sign in first. Click on your Apple ID, there is a popup asking for your password. After you done that, there is a row called "Computer Authorizations." If there are 5 computer that might mean that you can't authorize anymore computers and it might be the reason why you can't sync. I am not sure how you can deauthorize all the computers now after 7.0.1. There is a way on 6.0.5 but it is gone.
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