I restored/updated an old vers. ipod,but iTunes wont lemme transfer songs

i have a 20 MB old version clickwheel ipod
i restored it and updated it..
and all the songs on it erased (which is okay)
but now i have new songs (not from iTunes)
and iTunes won't let me transfer them to the ipod
the songs are in the correct format...
what do i do?!

You have to update to 10.6.8 first.
Then, if your machine qualifies, this explains how to get Mavericks:
http://www.apple.com/osx/
This explains whether your machine is capable of Mavericks installation:
http://support.apple.com/kb/HT5842

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