How do I transfer music between iTunes and iPod?
iPod offers three ways to transfer music from your iTunes 2 music library. You can select one of the following update modes from the iPod Preferences menu in iTunes: Update all music automatically. This is the default mode, in which iTunes copies your entire music library, including playlists, to iPod when you connect it to your Mac and deletes songs on iPod that are not listed in iTunes. If your iTunes library exceeds the iPod storage capacity, you will be prompted to select a different update method. Update selected playlists. With this option, iTunes automatically copies selected playlists to iPod whenever you connect to your Mac, and the songs on iPod that are not in the selected iTunes playlists are deleted. Update manually. You can also choose to transfer music to iPod manually. This enables you to drag and drop songs and playlists from iTunes to iPod. In the automatic and playlist synchronization modes, songs that are unchecked in iTunes are not transferred to iPod.