Help with syncing songs to Mac from iPod (unknown type and generation)

My brother got an iPod for Christmas, and my mom had downloaded songs from our aunt's computer. It works just fine, and he can charge it, but we want to put it on my mom's Mac. However, when I tried to transfer purchases from iPod, it said that 100 songs couldn't be transferred and none of the songs showed up on the playlist. My sister's birthday party is today, and we're going to play music with an iPod but I think it would be easiest to do it with just one iPod, and then my iPod could have his songs as well. Please help me! Thank you!

Do you mean that when you disconnect they dont show up?

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Do you mean that when you disconnect they dont show up?

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The following answers are based on the assumption that you automatically update. This means you will leave the iPod set to automatically have iTunes add songs (and you don't have to manually drag songs). This should be the default setting. To check, go to edit-->preferences with the iPod connected and hit the iPod tab.
1) It will add all songs. You can change this though. Connect the iPod (perhaps the first time you are syncing). Go to edit-->preferences. Hit the iPod tab. Select only update checked songs. Now any songs you uncheck are removed from the iPod or not synced at all.
2) If you have the option I talked about above checked, it will add all new songs that are checked automatically. By default, iTunes will want to have all new content added. But, if you have the only update checked songs option enabled, then only new songs that are checked will be updated.
3) New playlists automatically sync to the iPod. If you change older playists, these changes will be reflected on your iPod the next time you sync.
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Help with syncing songs to Mac from iPod (unknown type and generation)

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