Trouble Copying Songs from Mac to iPod

I recently purchased a new MacBook Pro.
I copied my iTunes folder from my PowerBook to my MacBook Pro. All of my songs appear in the library.
I have my iPod set up to manually manage my songs.
When I copy songs from library to my iPod, they don't copy. I don't even get a warning message. I did the reset warnings on my iPod and still no message.
If I go to my iMac computer, I can copy songs from iTunes to my iPod with no problem
Why can't I copy songs from my new MacBook Pro to iTunes?
I have reset my iPod, my sure I am running latest versions of the software etc.
MacBook Pro, 2.1 GHz   Mac OS X (10.4.7)   2 GB Ram

Shooting from the hip, I'd say try running a restore with the iPod connected to the new MacBook.
Good luck.

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