ITunes and Ipod won't synch up

AQfter a computer issue I was able to salvage all of my songs from ipod back to computer. With all of the changes I had to make to my settings I can't seem to figure out how to get those songs to synch up with the ipod.
When I plug my ipod in, it no longer updates, and the upadte ipod option is shaded. How do I turn this back on?

Can you post a screenshot or provide all the specs of the video's Summary tab so we can compare them with what is compatible with the 5G iPod.
B-rock

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