Why wont my new ipod sync my enitre library?

I've been trying to sync my entire library to a new iPod but nothing is working. Even dragging and dropping individual songs won't work. What am I doing wrong??

plug device into computer- open itunes - click name of device- click music tab- uncheck sync music at top- apply at bottom.  now check sync music at top -entire librarty- apply at bottom
if no result right click on a few songs and create aac version- sync again
Peace, Clyde

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