To upload songs to iPod from your iTunes music library, you must…

...Connect your iPod to your computer using your USB 2.0 cable and iTunes should automatically recognize your iPod and depending on whether or not you have the "Automatically update songs" option on, your iPod will start synchronizing the songs from iTunes.

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If that feature is off, go to 'File > Sync iPod’, and songs in your iTunes library will be downloaded on your iPod.

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Updating Your iPod Manually Using iTunes

If you have an extensive iTunes library you may want to update your iPod manually. Connect your iPod to your computer.

Open iTunes and click on ‘Users iPod’ under ‘Devices’ on the left hand side of iTunes user interface.

Click on 'Summary' and you will see the details of your iPod, its 'Version' and 'Options'. Under ''Options' check the box that says 'Manually manage music and videos'.

A dialog box will appear saying that "are you sure you want to manually manage music and videos on your iPod" in which you should click 'OK'.

Note: You will need to manually eject your iPod from your computer before it can be disconnected safely if you choose to manage your songs manually.