Ipod won't download latest purchase

Ipod model PE971LL

13.0 GB available

Connected to the computer through its charging cable. The computer recognizes the connection. iTunes connects the Ipod and warns to eject before disconnecting.

I've pressed sync multiple times, dragged the album onto the Ipod's music library, tried dragging individual songs, multiple songs... nothing will load onto it. What gives?

Edit: And I've restarted it.