HT3951 I have a 3rd generation ipod nano and I recently downloaded itunes version 1.1.3. my computer recognizes my ipod and says it's connected, but it won't sync some new songs I just downloaded. why not?

Why can't I sync my ipod? and where is the newest sync button? there is no more file and sync button anymore.

Are you sure you have a 2G iPod? See:
Identifying iPod models
A 2G can go to iOS 4.2.1 via iTunes directly if you have iTunes 10.X on your computer.
A 1G can go to 2.2 via iTunes amd 3.1.3 via the link proved already in this discussion.
Error 1 or -1
This may indicate a hardware issue with your device. Follow Troubleshooting security software issues, and restore your device on a different known-good computer. If the errors persist on another computer, the device may need service.
From:
http://support.apple.com/kb/TS3694#error1

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