Ipod wont cyns properly

When i conect my ipod nano second generation it says updating it completes update but without putting the song in my libary onto my nano

in setting i have "sync all music from libary" checked

what wrong

thanks in advance

Make sure its checked off and double check your setting. Is the file type supported on your iPod?

iv done that its something that is not obviouse that is wrong with it

This may be of help

http://www.apple.com/support/ipod/five_rs/

It helps to reinstall sometimes when things start behaving strangly