While in the folder of the iPod accessed from "My Computer", go to the menu bar and go to Tools--->Folder options while in a folder and make sure that "Show hidden files" is checked. If it is not, check it and apply the changes. On some models of the iPod, the music directory for the music is hidden.
If the above does not work, you can try the program "iFunBox". It is a file program for the iPod Touch and iPod Phone, but may also work for the 5th Gen Nano since they were made close to the same time period, assuming the file setup and compatibility is similar.
Have a great day!
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