Music from CDs that is on my iPod won't transfer to my iTunes library on a different computer I used to use but all music bought from iTunes will? How do I fix this?

In the past to get music from CDs onto my iTunes library and onto my iPod was all easy and fine, as you would know if you have done such a thing before. I used to use a different laptop for all my music stuff to the desktop I have to use now as the other one is broken. It is an authorised computer on my iTunes, so my issue has got nothing to do with that. When I got this desktop (it is quite an old one, if that makes any difference), i had to download iTunes and put all my music into my library to back it up.
However, all music that I had bought physically that is currently on my iPod (CDs) WON'T transfer into my new library on the desktop, but all music that I had bought digitally (iTunes) WILL transfer.
This has led to about 300 missing songs in my library and means I can't transfer all of my music onto a different device (as I am trying to transfer all my music onto an iPhone 3).
I have tried countless things. All of that "File > Devices > Transfer purchases" stuff WILL. NOT. WORK. I tried copying the music into a file on the desktop and then adding said file into the library, but it won't let me paste any music.
If someone were to help me in transferring the music I so dearly love then I would be eternally grateful.
Thank you

See Recover your iTunes library from your iPod or iOS device.
tt2

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