System Rebuild - Cannot sync purchased songs with IPOD

I recently had to rebuild my laptop, starting with the OS (Yes, it is a Windows machine . Before I did this, I copied all of my songs out of my music folder onto an external drive.
I thought that is what I would need to do. But I sense that there is more to it.
Upon rebuild, I copied all of those songs into the new my music folder. When I opened Itunes...they were all there. All 1233 of them. However, after syncing with my IPOD...it would only sync the songs that came from CD. All that were purchased are not on my IPOD. They remain in my itunes folder.
Does anyone know what I need to do? We are talking approximately 350 songs that I have purchased on Itunes...so it is substantive.
Any help would be appreciated. Thanks.

Did you reauthorise your PC after you restored Windows and reloaded iTunes? Do the songs themselves play in iTunes? For more on authorising have a look at this page:
About iTunes Music Store Authorisation and Deauthorisation

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