You can sync audiobooks, podcasts, and iTunes U content from your iTunes library with your iPod, iPhone, or iPad. You can sync an iPhone with only one computer and iTunes library at a time.
Note: Buttons for additional panes appear in iTunes depending on the types of content in your iTunes library.
If you have more content than can fit on your device, iTunes offers to create a special playlist to sync with your device. iTunes fills the playlist with selections from your library; you can change the contents of the playlist and sync again.
To add podcasts to your iPod, iPhone, or iPad:
Connect your iPod, iPhone, or iPad to your computer.
When your device appears in iTunes (below Devices), select it.
Click the Podcasts button and do one of the following:
To automatically update your iPod, iPhone, or iPad with all the podcasts in your Podcasts playlist, select Sync Podcasts.
To automatically update your iPod, iPhone, or iPad with selected podcasts, select Sync Podcasts and select your sync options.
To add podcasts to your iPod, iPhone, or iPad manually, deselect Sync Podcasts and drag podcasts or podcast episodes from your Podcasts playlist to the iPod, iPhone, or iPad icon in the iTunes window.
If you have an iPod shuffle (1st or 2nd generation) or a third-party music player, you can only add podcasts to it manually.
When you sync podcasts to your iPod, iPhone, or iPad, iTunes distinguishes between “New” and “Unplayed” podcasts. A “New” podcast is one that has never been played, and it’s indicated in the list of podcasts by a blue dot 
. An “Unplayed” podcast is one that’s never been played all the way through, and it’s indicated in the list by a blue half-dot 
.
To sync audiobooks or books with your iPod, iPhone, or iPad:
Connect your iPod, iPhone, or iPad to your computer.
In iTunes, select your iPod, iPhone, or iPad (below Devices), and click the Books button.
Select Sync Audiobooks, and do one of the following:
To sync all the audiobooks in your iTunes library to your device, choose “All audiobooks.”
To add selected audiobooks and playlists containing audiobooks, choose “Selected audiobooks and playlists,” and select the audiobooks and playlists you want to sync.
Click Apply.
To sync iTunes U content:
Connect your iPod, iPhone, or iPad to your computer.
When your device appears in the iTunes window (below Devices), select it.
Click the iTunes U button and select the items you want to sync.
Click Apply.
To sync ringtones (iPod touch 4th generation and iPhone only):
Connect your iPod touch or iPhone to your computer (make sure the iPhone has been activated).
When your device appears in the iTunes window, select it.
Click the Ringtones button and select the items you want to sync.
Click Apply.
For more information, see your device’s user guide or the Apple Support website.