2nd Gen Ipod will sync with itunes but will not download new song

Question

My Ipod will sync with itunes but will not download newly purchased songs.  It is Ipod nano 2nd gen.

Answer 1

If you want to use automatic syncing, you may need to set up or update the iPod's Music sync settings in iTunes.  If the new songs are not included in what gets synced to the iPod, they will not sync.
If the sidebar (along left side of window) is hidden, from the menu bar, under View, select Show Sidebar.  The iPod appears in the sidebar, under DEVICES.  Select it there, to show its Summary screen to the right.  Toward the top, there is a bar of buttons, starting with Summary.  Click on Music next to Summary.  This Music screen is where you tell iTunes how to sync songs to the iPod.
Check the box for Sync Music, if not already checked. This is the "switch" to enable automatic syncing for songs.
NOTE:  If Sync Music is not already checked, that means the iPod is currently set to Manually manage music.  Setting up automatic syncing will replace the iPod existing content.  If you want to add the new songs manually to the iPod (instead of using automatic syncing), please post back.
If your iTunes library fits on the iPod, you can choose the option to sync Entire music library.  Otherwise, choose the option to sync Selected playlists, artists, albums, and genres.  Below that, select (checkmark) what you want to sync to the iPod from the lists.
One convenient way to set this up is to first create one or more playlists in your iTunes library, with ALL of the songs you want on the iPod.  Or you can use existing playlists.  Back on the iPod's Music screen in iTunes, select those playlists under Playlists.
When you click Apply, iTunes syncs the songs in your selection(s) to the iPod (replacing its existing content).  Going forward, to update the iPod, you can just update those playlists in your iTunes library (add/remove songs).  If you have new songs, add them to a playlist that is synced to the iPod.  The iPod does not need to be connected.  The next time you connect the iPod (or click Sync if already connected), iTunes automatically updates your iPod with the same changes.