IPad won't sync with old iMac with new hard drive.

The new drive recognizes the iMac, and the photos on the iPad were successfully imported into iPhoto, but 2 home videos on the iMac will not transfer. I have tried to manually drag and drop, different cords and ports, over wi-fi, etc... The Summary box says the iPad has never backed up to this computer, but when I try to do that, it tries and then stops with no error message. The Movies tab has the two videos I want to transfer, but the sync button is gray. I have hard rebooted the iPad and restarted the iMac. Also deauthorized and reauthorized the iMac. I suspect that somehow the iPad is not recognizing the new hard drive. Is that possible? Any suggestions? Thank you for your help!

I don't mean the latest version of iOS.  I mean the latest version of iTunes on your Mac.
Open iTunes on your Mac.  Click Help and then Check For Updates

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