Can i use my ipod with this mac

Sorry if this was asked before, but my problem and question may be slightly different.
I have an old 20 gig ipod that I've had since 1995. I have downloaded many songs from i-tunes and from my own cd's to my pc running widows xp. There are about 1300 songs on the i-pod
The pc was given away to a friend who transferred all my music to my macbook. The hard drive was removed. We did not deauthorize the pc---(I know-a mistake).
I-tunes and everything works and plays ok on the Mac. Even new songs I've ordered or put in from cd's work & play ok. But note--in the "library" section not all the tunes have the little check in the box next to them. I do not know why this is. I have no problem synching from this Mac to my i-phone.
So--my question is---can I now use (synch) the ipod with this Mac ?
Can I just plug it in an keep using it to update my library ? I certainly do not want to erase all the tunes on it and not be able to replace them. What exactly do I have to do ?
Any help and detailed instructions would be greatly appreciated----Thanks---Jerry

I have a similar problem. I have a 60 GB old non video ipod. It connected to my old G5 with a firewire plug. Ihave been running it for eight or more years. When I upgraded to new IMAC and MacBook Pro 15 in. They do not have inputs for the end of the cradle. One end has the same wide flat connector now used by ipod touches. I have a new third gen IPOD touch. I was able to sync both ipods with both the two old computers and the two Snow Leopard macs. I must have accomplished by sharing in Itunes preferences.
It has been awhile. Anyhow, now I am trying to sync the oldest IPOD. It doesn't show up on my new IMAC as a device. I suppose because it isn't pluged in. I tried disconnecting my 1 T external hard drive to see if I could use that input. But I don't see any port to connect my older IPOD? How do I add music from CD to new IMAC and sync it onto the old IPOD. I feel so lame. Please someone. I have read lots of books on IPOD touch and IMAC Portable, Snow Leopard. Maybe I need to check them out of library or buy one. Please advise. Spinning wheels.

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