There are about 8 songs in a playlist on itunes that are listed in the playlist but cannot be transferred to my ipod because it states: "..the original file could not be found." When I try to locate the song I get a list of the different music librar

There are about 8 songs on a playlist that are listed in the playlist library but when I try to transfer them to the playlist, it states that they can't be transferred because the original file could not be found. Then it asks, do you want to locate the file but when I try that I get a few libraries but am not sure how to locate the particular songs. Some of the songs were purchased and some were transferred from a CD. I have seen the same question asked on the help page but haven't found an answer.
Thanks.

Hi dones49,
It sounds like your issue here is that iTunes can not find the files for some of the songs you have brought into it. This happens occasionally even if the songs have not been moved from the location that iTunes places them on import or purchase. When you try to use the song, iTunes prompts you to find the file, as you have seen.
To find the file, use the information in this article to navigate through the iTunes media folders -
Locate and organize your iTunes files
If you are still unable to locate the files, you may need to download them from the iTunes store again, or rip them from your CDs. See this article for assistance with downloading your past purchases -
Download past purchases
Thanks for using Apple Support Communities.
Best,
Brett L 

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