Having trouble Syncing my nano and shuffle using the same libary

I have only one libary but I have a iPod nano and a iPod shuffle. When I connect to itunes to sync my shuffle, everything goes well. Then I try to sync my nano but it does not sync. Yesterday I bought a album from the iTune store and I was able to sync the new songs into my Shuffle. I can not do that with my nano? Can someone help me understand what needs to be done? Both are carbon copys with the same songs. One my husband uses and I use the shuffle. I would appreciate any help

I get no error message. I first plug in my shuffle - everything syncs. Then I plug in the Nano, it just sits there. I go to the top and try to click on "sync ipod" but it is light gray and will not allow me to click on it.

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Having trouble Syncing my nano and shuffle using the same libary

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