iTunes 10 for Mac: Sync your device automatically
As your iTunes library changes, you can have iTunes make the same changes automatically on your iPod, iPhone, or iPad.
For example, say you import a lot of new songs into your iTunes library that you want on your iPod. Rather than having to remember which songs you added, and then adding them manually to your device, iTunes can sync all the new songs to your iPod automatically when you connect it to your computer.
If your iTunes library is too large to fit on your device, or if you don’t want to sync your entire library, you can select certain items to sync; for example, you can sync only the podcasts you haven’t yet listened to or all the songs in a certain playlist.
After you sync your device automatically, you can still drag individual items from your library to the device.
These instructions apply to Music, Movies, TV Shows, Podcasts, iTunes U, Books, and Tones. The types of media you can sync depends on the device you have.
To set up automatic syncing:
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Connect your iPod, iPhone, or iPad to your computer.
If this is the first time you’re connecting your device, see Set up your iPod, iPhone, or iPad.
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When your device appears in the list on the left side of the iTunes window (below Devices), select it.
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Click a button at the top of the iTunes window to select the type of media you want to sync.
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Select the Sync checkbox, and select the items you want to sync.
A blue dot
next to an item means it’s new (never been played). A blue half-dot 
means the item is unplayed (hasn’t been played all the way through). The capacity bar shows you how much space will remain on your device after you sync.
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When you’re ready to sync, click Apply.
Every time you sync, iTunes uses the same settings until you change them.
You can sync multiple devices with the same iTunes library, and use different settings for each device. iTunes saves the settings for each device. You can automatically sync a device with only one iTunes library at a time.
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