Click "Sync" to add your songs.
Whether you chose the manual or automatic option for adding songs, click the "Sync" (short for "Synchronize") button on the bottom right of the screen when you're ready to add your songs to your iPod. iTunes should immediately begin to add the songs you selected to your iPod
BTW, if you want to transfer music from iPod to iTunes, just check out this tutorial: https://www.leawo.org/tutorial/3-ways-to-transfer-music-from-ipod-to-itunes-library.html?=1400
You just need to import your song into iTunes library, then make a playlist with the songs, plug in your iPod to computer, iTunes will detect the iPod automatically, then click iTunes menu "File -> Sync iPod", the songs will be transferred from iTunes to iPod.
For more tips about iPod, you may refer to this iPod FAQ.
http://www.mac-dvd.com/ipod-tips-and-ipod-faq.html
Hope it helps. Contact me if you have any other question.
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