Trying to move iPod classic to new PC, won't sync or transfer purchases

I've already transferred the library from the old PC to the new PC, deauthorized the old PC and authorized the new PC. My son's ipod classic shows up in iTunes on the new pc, but when I click on either SYNC or TRANSFER PURCHASES, nothing happens. No alarms, no questions, nothing.
Any ideas? Need to get this done before he heads back to school next week.

If, as I think is the case, all your tunes are on your ipod not on your new laptop then you need to copy them from ipod->laptop.
Google 'itunes computer copy' for example, to find a program to do it. Other words might work 'ipod computer copy'?

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