Select the iPod nano tab in the iTunes window and click the tabs at the top of the iPod Settings window. Each tab represents different content that may be synced to your device. Check the boxes next to "Sync Music," "Sync Videos" and "Sync Audiobooks" to set up automatic synchronization of content in your iTunes' library.
Click the "Apply" button at the bottom of the iTunes window to save the new synchronization settings. Wait for the iPod nano to display a "Safe to disconnect" message on its screen. Once the message is displayed, it is safe to unplug the device from the computer.
Select the empty check box next to "Manually manage music and video" in the Summary section in iTunes.
The iPod model A1285, also known as the 16GB iPod nano Chromatic, was released in 2008 as part of the iPod nano Chromatic series that offered a variety of colors and a new design to the device, according to the official Apple website (see the Resources section). Like other iPods, the iPod nano uses the iTunes program to sync content from your computer and supports audio and video playback. With 16 gigabytes (GB) of storage space, the iPod nano Chromatic is able to carry your entire iTunes library through automatic synchronization or allows you to manually add content to the device.
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