Transferring music from iPod to itunes/iPhone?

[Goose]

My dad has an old iPod nano that has some music on it bought digitally and some that he imported on from CD's a few years ago. He has an iPhone 6 and he'd like to have all his music on that so he can ditch the iPod nano but we've both failed at accomplishing that. The stuff bought digitally has transferred fine but the bulk of it hasn't, presumably because it's all the CD stuff.

Is it literally impossible to have music from CD's in your iTunes library, forcing you to have to buy it all again?

Thanks

 

[Goose]

Can't you just plug the iPhone into the PC so it acts as a USB drive and copy and paste it over?

With the way the iPod is formatted it would seem not as there aren't any actual individual tracks to copy.