ITunes is always the primary choice when it comes to transferring music from iPod to iPhone on your Mac. You can use iTunes to transfer the purchased albums back to iTunes Music Library, and then sync them to iPhone. Please note that if you have hundreds of thousands of songs in iTunes Music Library, you'd better create a separate playlist for the songs you want to transfer. Then you can choose the playlist when you sync music to iPhone with iTunes.
1. Transfer Purchased songs from iPod to iTunes Music Library.
2. Connect iPhone to Mac with USB cable.
3. Click the iPhone icon and choose Music.
4. Check Sync Music, and choose the iPod music playlist.
5. Click Sync at the right bottom.
3 Ways to Transfer Music from iPhone to iPad
That is sign of frustration. you need to have i tunes installed on your laptop once you do this i tunes will check for any music on your computer and then you can sink the i phone I have the same combo, if you really get frustrated, call apple support they are very good at helping out with these kind of problems and most of the time its free. good luck
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